Boron tribromide → HCID 58543823, compound

HRID 1673280Notes

Reaction equation

HRID 1673280 reaction equation
[F: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])=[CH:4][C:3]=1[O:31]C.B(Br)(Br)Br>ClCCl>[F: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:13])([F:12])[F:14])[OH:10])=[CH:4][C:3]=1[OH:31]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58543912HCID 58543912, compound

Product 1

HCID 58543823HCID 58543823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Analogously to example 10 42 mg (0.09 mmol) 4-fluoro-α-[(ethylsulfanyl)methyl]-3-methoxy-β-[(2-methylquinolin-5-yl)amino]-α-(trifluoromethyl)benzeneethanol in 1.7 ml dichloromethane are treated with 0.9 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 28 mg of the desired product.

Sources & evidence

ORD record
ord-f2741575a0e14114a5420b5156ed63a9
Source dataset
uspto-grants-2011_08
Patent number
US07999108B2

Reaction notes

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