Boron tribromide → HCID 24781011, compound

HRID 420623Notes

Reaction equation

HRID 420623 reaction equation
[F:1][C:2]1[C:3]([O:33]C)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([NH:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]3[C:15]=1[CH:16]=[N:17][C:18]([CH3:25])=[N:19]3)[C:7]([C:27]([F:30])([F:29])[F:28])([OH:26])[CH2:6][C:5]2([CH3:32])[CH3:31].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[CH:8]([NH:13][C:14]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]4[C:15]=3[CH:16]=[N:17][C:18]([CH3:25])=[N:19]4)[C:7]([C:27]([F:28])([F:29])[F:30])([OH:26])[CH2:6][C:5]([CH3:31])([CH3:32])[C:4]=2[C:3]=1[OH:33]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66657416HCID 66657416, compound

Product 1

HCID 24781011HCID 24781011, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

111.2 mg (0.231 mmol) of (rac.) 6-fluoro-1-[(8-fluoro-2-methylquinazolin-5-yl)-amino]-5-methoxy-4,4,7-trimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-ol is mixed at 0° C. with 3.2 ml of a 1 molar solution of boron tribromide in dichloromethane, and it is stirred for one and one-half hours at 0 to 5° C. At 0° C., the now carefully saturated sodium bicarbonate solution is added in drops. After 10 minutes of vigorous stirring at room temperature, the batch is extracted three times with ethyl acetate. The organic phases are dried, and the residue is chromatographed on a Flashmaster after the solvent is spun off. 66.4 mg (61.5%) 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 ethyl acetate
  3. customThe organic phases are dried
  4. customthe residue is chromatographed on a Flashmaster after the solvent

Sources & evidence

ORD record
ord-9e6774593823419cb9021b9cc9353c7c
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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