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
3
Procedure
Treat 5-fluoro-1H-indole-2-carboxylic acid 3 (X═F, 1.7 g, 9.5 mmol) with piperidine as described in General Synthetic Procedure VIa to afford 5-fluoro-1H-indol-2yl-piperidin-1-yl-methanone 8 (X═F, R4=piperidin-1-yl; 2.3 g, 100%) as a white solid. 1H NMR (DMSO-d6) δ 11.7 (brs, 1H), 7.5-7.3 (m, 2H), 7.1-7.0 (m, 1H), 6.7 (s, 1H), 3.7 (m, 4H), 1.7-1.5 (m, 6H). Treat 5-fluoro-1H-indol-2yl-piperidin-1-yl-methanone (125 mg, 0.51 mmol) with 2-aminophenyldisulfide (347 mg, 1.4 equiv.) as described in General Synthetic Procedure VIIa to afford the title compound Iac (92 mg, 25%) as an ivory-colored solid, m/z=369 (M+1).
Sources & evidence
- ORD record
- ord-b01dddf72c80499ba10e070118c37313
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008340B2
Reaction notes
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