Boron tribromide → HCID 86600870, compound

HRID 420619Notes

Reaction equation

HRID 420619 reaction equation
[F:1][C:2]1[C:3]([O:32]C)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=1[CH:16]=[CH:17][NH:18][C:19]3=[O:24])[C:7]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:6][C:5]2([CH3:31])[CH3:30].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[C:3]([OH:32])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=1[CH:16]=[CH:17][NH:18][C:19]3=[O:24])[C:7]([OH:29])([C:25]([F:28])([F:26])[F:27])[CH2:6][C:5]2([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66657350HCID 66657350, compound

Product 1

HCID 86600870HCID 86600870, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

59.7 mg (0.128 mmol) of (rac.) 5-{[6-fluoro-2-hydroxy-5-methoxy-4,4,7-trimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-isoquinolin-1-(2H)-one is mixed at 0° C. with 1.3 ml of a 1 molar solution of boron tribromide in dichloromethane, and it is stirred for one hour at 0 to 5° C. At −10° C., saturated sodium bicarbonate solution is now carefully added in drops. After 10 minutes of vigorous stirring at room temperature, the batch is extracted three times with methyl-tert-butyl ether. The organic phases are dried, and the residue is chromatographed on a Flashmaster after the solvent is spun off. 46.5 mg (80.3%) of the desired compound is isolated.

Workup

  1. stirringAfter 10 minutes of vigorous stirring at room temperature
  2. extractionthe batch is extracted three times with methyl-tert-butyl ether
  3. customThe organic phases are dried
  4. customthe residue is chromatographed on a Flashmaster after the solvent

Sources & evidence

ORD record
ord-727cd187a2ae412da920a7e875c9fc1e
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

Loading…