2-Bromo-4-methylanisole → 5-chloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Cl:11][C:12]1[CH:13]=[C:14]2[C:20](=[O:21])[C:19](=[O:22])[NH:18][C:15]2=[N:16][CH:17]=1>>[Cl:11][C:12]1[CH:13]=[C:14]2[C:20]([OH:21])([C:2]3[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=3[O:9][CH3:10])[C:19](=[O:22])[NH:18][C:15]2=[N:16][CH:17]=1

Participants

Reactant 2

HCID 891432-Bromo-4-methylanisole

HCID 674305355-chloro-1H-pyrrolo[2,3-b]pyridine-2,3-dione

Product 1

HCID 674301815-chloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneYield 81.9%

Procedure

With 1.49 g of 2-bromo-4-methyl anisole and 900 mg of the compound obtained in Step 118-4 as starting materials, 1.23 g of the title compound (brown solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record: ord-8e71cc0f4c8545c184221b8d1d01a314
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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