Boron tribromide → HCID 58543889, compound

HRID 1921583Notes

Reaction equation

HRID 1921583 reaction equation
[F:1][C:2]1[C:7]([O:8]C)=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[CH:11]([NH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2)[C:12]([CH2:18][S:19][CH2:20][CH3:21])([C:14]([F:17])([F:16])[F:15])[OH:13].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[CH:11]([NH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2)[C:12]([CH2:18][S:19][CH2:20][CH3:21])([C:14]([F:16])([F:15])[F:17])[OH:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58543870HCID 58543870, compound

Product 1

HCID 58543889HCID 58543889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Analogously to example 10 40 mg (0.08 mmol) 2,4-difluoro-α-[(ethylsulfanyl)methyl]-3-methoxy-β-[(2-methylquinolin-5-yl)amino]-α-(trifluoromethyl)benzeneethanol in 1.6 ml dichloromethane are treated with 0.8 ml of a 1 M solution of boron tribromide in dichloromethane at −20° C. The typical work up after 22 hours at room temperature and chromatography on silica gel (acetone in hexane 50%) yields 26 mg of the desired product.

Sources & evidence

ORD record
ord-c174f1c957b542dda63d4d51749ca079
Source dataset
uspto-grants-2012_05
Patent number
US08173676B2

Reaction notes

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