Boron tribromide → HCID 24781011, compound

HRID 1443288Notes

Reaction equation

HRID 1443288 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., 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 ethyl acetate. The organic phases are dried, and after the solvent is spun off, the residue is chromatographed on a Flashmaster. 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

Sources & evidence

ORD record
ord-db765cd14c0848d6817aed765fa7046c
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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