Boron tribromide → HCID 11328179, compound

HRID 1444408Notes

Reaction equation

HRID 1444408 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31]C)=[C:6]([C:8]([CH3:30])([CH3:29])[CH2:9][C:10]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH:11]=[N:12][C:13]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]3[C:14]=2[CH2:15][NH:16][C:17]3=[O:23])[CH:7]=1.B(Br)(Br)Br.CO.ClCCl>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:31])=[C:6]2[C:7]=1[CH:11]([NH:12][C:13]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]3[C:14]=1[CH2:15][NH:16][C:17]3=[O:23])[C:10]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH2:9][C:8]2([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 17985049HCID 17985049, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 11328179HCID 11328179, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

380 mg (0.832 mmol) of 4-{[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidene]amino}6-fluoro-2,3-dihydroisoindol-1-one is mixed at room temperature with 8.3 ml of a 1 M solution of BBr3 in dichloromethane and stirred for one hour at ice bath temperature. The working-up of the batch is carried out as described in Example 4. After chromatography of the crude product on a Flashmaster (amine phase; mobile solvent methanol/dichloromethane), 9.2 mg (2.7%) of the desired compound is obtained.

Sources & evidence

ORD record
ord-adc4da394f3c4437865898627466d685
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

Loading…