Boron tribromide → HCID 19597403, compound

HRID 611546Notes

Reaction equation

B(Br)(Br)Br.[NH2:5][C:6]1[C:7]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:17]([O:30]C)[CH:16]=3)=[CH:13][N:12]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:8]=2[N:9]=[CH:10][N:11]=1>ClCCl>[NH2:5][C:6]1[C:7]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:17]([OH:30])[CH:16]=3)=[CH:13][N:12]([CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of boron tribromide in dichloromethane (0.9 ml of a 1M solution) was added dropwise with stirring to a solution of the product from Example 32, N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide (130 mg) in dichloromethane (6 ml) at -10° C. under nitrogen, after the addition the reaction mixture was allowed to warm to 0° C. and stirred at 0° C. for 1.5 hours. The reaction mixture was quenched by the dropwise addition of saturated aqueous sodium bicarbonate solution (5 ml) at 0° C. There was an exotherm and the temperature of the mixture rose to 10° C. The mixture was allowed to warm to ambient temperature, then extracted with dichloromethane to give N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzamide, m.p. 173-175° C. (with decomposition). The structure was confirmed by 1H nmr and mass spectra.

Workup

additionafter the addition the reaction mixture
customThe reaction mixture was quenched by the dropwise addition of saturated aqueous sodium bicarbonate solution (5 ml) at 0° C
customrose to 10° C
temperatureto warm to ambient temperature
extractionextracted with dichloromethane

Sources & evidence

ORD record: ord-e63d59bc6c164be1b6f7ee31ac2ab468
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001839

Reaction notes

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