5-Fluoroindole-2-carboxylic acid → HCID 9035231, compound
Reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[NH:7]1[C:8]2[C:4](=[CH:3][CH:2]=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13]Participants
Procedure
Treat 1H-indole-2-carboxylic acid 3 (X═H, 750 mg, 4.66 mmol) with piperidine (3.0 equiv., 1.4 mL, 13.98 mmol) as described in General Synthetic Procedure VIa to afford 1H-indol-2yl-piperidin-1-yl-methanone 8 (X═H, R4=piperidin-1-yl; 979 mg, 92%) as a white solid, mp 161-162° C. 1H NMR (DMSO-d6) δ 11.5 (s, 1H), 7.6 (d, 1H), 7.4 (d, 1H), 7.2 (t, 1H), 7.1 (t, 1H), 6.7 (s, 1H), 3.7 (m, 4H), 1.7-1.5 (m, 6H). Treat 1H-indol-2yl-piperidin-1-yl-methanone (456 mg, 2.0 mmol) with phenyldisulfide (480 mg, 2.2 mmol) as described in General Synthetic Procedure VIIa to afford the title compound Ix (440 mg, 65%) as an opaque oil. 1H NMR (DMSO-d6) δ 12.1 (brs, 1H), 7.5 (d, 1H), 7.4 (d, 1H), 7.3-7.1 (m, 3H), 7.1-7.0 (m, 4H), 6.7 (s, 1H), 3.6 (m, 2H), 3.4 (s, 8H), 3.2 (m, 2H), 1.8 (m, 4H), 1.4 (m, 2H). m/z=337 (M+1).
Sources & evidence
- ORD record
- ord-6fbd3eec13c54ebcad8b05c85a2dbd57
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008340B2
Reaction notes
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