Boron tribromide → 1-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

HRID 2106017Notes

Reaction equation

HRID 2106017 reaction equation
[OH:1][C:2]([C:32]([F:35])([F:34])[F:33])([CH2:15][C:16]([C:19]1[CH:24]=[C:23]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:22]=[CH:21][C:20]=1[O:30]C)([CH3:18])[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1.B(Br)(Br)Br>C(Cl)Cl>[OH:1][C:2]([C:32]([F:35])([F:34])[F:33])([CH2:15][C:16]([C:19]1[CH:24]=[C:23]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:22]=[CH:21][C:20]=1[OH:30])([CH3:18])[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 578098941-[2-hydroxy-4-(2-methoxy-5-thiophen-3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Product 1

HCID 578097931-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-hydroxy-4-(2-methoxy-5-thiophen-3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (32 mg, 0.06 mmol) in methylene chloride (1 mL) at 0° C. under an argon atmosphere was added BBr3 (0.06 mL, 0.6 mmol). The mixture was warmed to room temperature, stirred 3 hours, cooled to 0° C., stirred 2 days, and quenched with methanol (5 mL). The volatiles were removed in vacuo and the residue diluted with ethyl acetate (10 mL), washed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL), and dried over magnesium sulfate. The volatiles were removed in vacuo and the residue purified by reverse phase HPLC to afford 1-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (20 mg, 68%).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred 2 days
  3. customquenched with methanol (5 mL)
  4. customThe volatiles were removed in vacuo
  5. additionthe residue diluted with ethyl acetate (10 mL)
  6. washwashed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe volatiles were removed in vacuo
  9. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-59e523f5dabd409481464abf1f0ae6cb
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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