5-Fluoroindole-2-carboxylic acid → HCID 9035231, compound

HRID 1677810Notes

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

Reactant 2

HCID 18205-Fluoroindole-2-carboxylic acid

HCID 8082Piperidine

Product 1

HCID 9035231HCID 9035231, compoundYield 92%

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. Treat 1H-indol-2yl-piperidin-1-yl-methanone (116 mg, 0.51 mmol) with 2-aminophenyldisulfide (347 mg, 1.4 equiv.) as described in General Synthetic Procedure VIIa to afford the title compound Iab (103 mg, 29%) as a tan solid, m/z=352 (M+1).

Sources & evidence

ORD record: ord-90fc8bb7debc44388458e0812e0ca484
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008340B2

Reaction notes

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