N-methyl-2-pyrrolidone → 4-(2-Phenylethyl)-1H-pyrazolo[3,4-b]pyridin-3-ol

HRID 2223947Notes

Reaction equation

Br[C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:21][NH2:22].CN1CCCC1=O>O>[C:14]1([CH2:13][CH2:12][C:6]2[CH:5]=[CH:4][N:3]=[C:2]3[NH:21][N:22]=[C:8]([OH:9])[C:7]=23)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-3-methoxycarbonyl-4-(2-phenylethyl)pyridine (1.42 g), hydrazine monohydrate (0.65 mL) and N-methylpyrrolidone (10 mL) was stirred at 100° C. for 2 hours. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration, washed with water and dried under reduced pressure to give the title compound (0.74 g).

Workup

filtrationthe precipitated crystals were collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-350e79f10242456c9d25fe5bdb8b79f2
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375113B2

Reaction notes

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