Trifluoroacetic acid → HCID 86698615, compound

HRID 1054611Notes

Reaction equation

HRID 1054611 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][C:27]=3[Cl:28])[NH:24][CH:23]=[C:22]4[C:29]([OH:31])=[O:30])=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:28][C:27]1[CH:26]=[C:25]2[C:21]([C:22]([C:29]([OH:31])=[O:30])=[CH:23][NH:24]2)=[CH:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698614HCID 86698614, compound

Product 1

HCID 86698615HCID 86698615, compoundYield 129.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (15 mg, 0.0341 mmol) in dichloromethane (2 mL) was added TFA (0.213 g, 1.87 mmol) and the resulting mixture was stirred for 45 min at room temperature. The reaction mixture was concentrated in vacuo to give 6-chloro-5-[4-(pyrrolidin-3-yl)phenyl]-1H-indole-3-carboxylic acid (15 mg) as an off-white solid. MS (ES+) 341.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 11.99 (br, 1 H), 8.92 (br, 1 H), 8.09 (d, 1 H), 7.94 (s, 1 H), 7.65 (s, 1 H), 7.43 (m, 4 H), 3.70 (m, 1 H), 3.50 (m, 4 H), 3.17 (m, 1 H), 2.04 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-04a18949ba9e428ba2e51847c80532fe
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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