Compound 8

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Compound data: HPLC

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of 7 (0.31 mmol, 116.0 mg) in AcOD-d4 (1.5 ml) was added Pd (OAc)₂ (0.31 mmol, 70.3 mg), and the resulting suspension was stirred for 1 h at 70 C. The reaction mixture was cooled to room temperature and purified by flash chromatography using DCM/MeOH as eluent to afford 8 (70.0 mg, 44%) as a red solid. Stereochemistry was confirmed by X-Ray analysis of the crystal obtained using chloroform/pentane as recrystallization solvents. ¹H NMR (600 MHz, CDCl₃): δ 8.13 (s, 1H), 7.60 (s, 1H), 7.59 (br s, 2H), 4.64 (s, 1H), 4.56 (q, J = 6.7 Hz, 1H), 3.82 (dq, J = 14.1, 7.1 Hz, 1H), 3.72 (dq, J = 13.9, 6.8 Hz, 1H), 3.22 (dq, J = 13.6, 6.6 Hz, 1H), 2.89 (dq, J = 13.7, 6.7 Hz, 1H), 1.40 (s, 9H), 1.22 (d, J = 6.8 Hz, 3H), 1.15 (t, J = 7.1 Hz, 3H), 1.10 (t, J = 7.1 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 171.79, 162.36, 155.27, 130.08 (q, J = 3.4 Hz), 129.82 (q, J = 3.5 Hz), 125.59 (q, J = 33.2 Hz), 125.15, 124.00 (q, J = 271.6 Hz), 80.18, 44.64, 41.16, 38.02, 28.16, 25.45, 21.73, 14.24, 12.85. ¹⁹F NMR (376 MHz, CDCl₃): δ –62.77. HRMS (ESI-TOF): m/z calculated for C₂₀H₂₈ClF₃N₂ONaPd⁺ [M+Na] ⁺ 533.0769, found 533.0771.