Hydrochloric Acid → 6-(Difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine hydrochloride

HRID 1475445Notes

Reaction equation

C(OC([N:8]1[C:16]2[CH:15]=[C:14]([C:17]([F:25])([F:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:27])([CH3:26])[CH2:9]1)=O)(C)(C)C.[ClH:28]>CO>[ClH:28].[F:25][C:17]([F:24])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:14]1[N:13]=[CH:12][C:11]2[C:10]([CH3:27])([CH3:26])[CH2:9][NH:8][C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 6-(difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (6.22 g, 16.6 mmol), methanol (30 mL) and hydrochloric acid (5M, 30 mL) was stirred at 20° C. for 3 h, at 35° C. for 4 h, then left at 20° C. for 14 h. Mixture was evaporated in vacuo and the residue azeotroped with toluene (×3), isopropanol and methanol (×3). Residue was dried in vacuo at 50° C. for 4 h to give the title compound. MS: [M+H]+=275.

Workup

waitleft at 20° C. for 14 h
customMixture was evaporated in vacuo
customthe residue azeotroped with toluene (×3), isopropanol and methanol (×3)
customResidue was dried in vacuo at 50° C. for 4 h

Sources & evidence

ORD record: ord-50b4a2546dc54c1f9bb6e59fbe81c0c7
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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