Boron tribromide → HCID 58543975, compound

HRID 1921579Notes

Reaction equation

HRID 1921579 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:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][C:31]([CH3:37])=[N:32]2)[C:12]([CH2:18][S:19][C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1)([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:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][C:31]([CH3:37])=[N:32]2)[C:12]([CH2:18][S:19][C:20]1[N:21]=[CH:22][CH:23]=[CH:24][N:25]=1)([C:14]([F:17])([F:16])[F:15])[OH:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58543903HCID 58543903, compound

Product 1

HCID 58543975HCID 58543975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Analogously to example 10 59 mg 2,4-Difluoro-α-{[(pyrimidin-2-yl)sulfanyl]methyl}-3-methoxy-β-[(2-methylquinolin-5-yl)amino]-α-(trifluoromethyl)-benzeneethanol in 5 ml dichloromethane are treated with 4.4 ml of a 1 M solution of boron tribromide in dichloromethane at −30° C. The typical work up after 22 hours at room temperature and chromatography on silica gel (acetone in hexane 10-50%) yields 44 mg of the desired product.

Sources & evidence

ORD record
ord-270ebaab493f4e6ab45f4e6e88d848ba
Source dataset
uspto-grants-2012_05
Patent number
US08173676B2

Reaction notes

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