Boron tribromide → HCID 58543921, compound

HRID 1921587Notes

Reaction equation

HRID 1921587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[CH:23][C:24]([CH3:30])=[N:25]3)[C:9]([CH2:15][S:16][CH2:17][CH3:18])([C:11]([F:14])([F:13])[F:12])[OH:10])=[C:4]([F:31])[C:3]=1[O:32]C.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[CH:23][C:24]([CH3:30])=[N:25]3)[C:9]([CH2:15][S:16][CH2:17][CH3:18])([C:11]([F:12])([F:14])[F:13])[OH:10])=[C:4]([F:31])[C:3]=1[OH:32]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58543950HCID 58543950, compound

Product 1

HCID 58543921HCID 58543921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Analogously to example 10 44 mg (0.087 mmol) 4-chloro-2-fluoro-α-[(ethylsulfanyl)methyl]-3-methoxy-β-[(2-methylquinolin-5-yl)amino]-α-(trifluoromethyl)benzeneethanol in 1.7 ml dichloromethane are treated with 0.87 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 30 mg of the desired product.

Sources & evidence

ORD record
ord-5608746827a64e1c8a679f99ed5013e8
Source dataset
uspto-grants-2012_05
Patent number
US08173676B2

Reaction notes

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