Water → 3-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 2205963

Reaction equation

[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)N=C(O[Si](C)(C)C)C.C1C(=O)N([Br:35])C(=O)C1.O>CN(C=O)C>[Br:35][C:8]1[C:9]2[C:10](=[O:15])[NH:11][CH:12]=[CH:13][C:14]=2[N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g).

Workup

temperatureto be cooled to room temperature
customat room temperature
stirringThe reaction mixture was stirred overnight at room temperature
stirringthe mixture was stirred at room temperature for 2 hr
filtrationThe white precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-f96fa7a44c5d4f9cb7b5f2f9ff9ae4cd
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Linked notes

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