Boron tribromide → HCID 11475767, compound

HRID 1869335Notes

Reaction equation

HRID 1869335 reaction equation
[F:1][C:2]1[C:11]([O:12]C)=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:31])([CH3:30])[CH2:5][C:6]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH:7]2[NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][NH:18][C:19]2=[O:24].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:31])([CH3:30])[CH2:5][C:6]([OH:29])([C:25]([F:27])([F:28])[F:26])[CH:7]2[NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][NH:18][C:19]2=[O:24]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68680359HCID 68680359, compound

Product 1

HCID 11475767HCID 11475767, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

109.8 mg (0.250 mmol) of (rac.) 4-{[5-fluoro-2-hydroxy-6-methoxy-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-2,3-dihydroisoindol-1-one is mixed with 3.4 ml of a 1 M solution of BBr3 in dichloromethane and stirred for four hours at room temperature. The batch is mixed at 0° C. with saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic extracts are dried on sodium sulfate. After the desiccant is filtered off, and after the solvent is spun off, the residue is chromatographed on a Flashmaster. 15.6 mg (14.7%) of the final product is isolated.

Workup

  1. extractionextracted twice with ethyl acetate
  2. customThe combined organic extracts are dried on sodium sulfate
  3. filtrationAfter the desiccant is filtered off
  4. customthe residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-659b5388aa4f4bb9b8e313aa2a395dc1
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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