Hydrochloric Acid → 6-chloro-5-[4-(pyrrolidin-2-yl)phenyl]-1H-indole-3-carboxylic acid

HRID 1054768Notes

Reaction equation

HRID 1054768 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[Cl:28])[NH:24][CH:23]=[C:22]3[C:29]([OH:31])=[O:30])=[CH:15][CH:14]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[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:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866987595-{4-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid

Product 1

HCID 866987606-chloro-5-[4-(pyrrolidin-2-yl)phenyl]-1H-indole-3-carboxylic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (140 mg, 0.318 mmol) in ethyl acetate (10 mL) was added hydrogen chloride in ethyl acetate (4 N HCl in EtOAc, 10 mL) under nitrogen. The suspension was stirred for 4.5 hours at room temperature. The mixture was concentrated to afford the desired product (100 mg, 83.5% yield). MS (ES+) 341 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.10 (s, 1H), 7.95 (s, 1H), 7.66 (s, 1H), 7.62 (d, 2H), 7.52 (d, 2H), 4.60 (s, 1H), 3.35 (s, 4H), 2.49 (m, 2 H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-d41ab3055ee24addadef1cb905c68b42
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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