Ethyl Acetate → HCID 58543938, compound

HRID 1921576Notes

Reaction equation

HRID 1921576 reaction equation
[Cl:1][CH2:2][C:3]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH:4]([NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]2)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([O:12]C)[C:6]=1[F:14].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[Cl:1][CH2:2][C:3]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH:4]([NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]2)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([OH:12])[C:6]=1[F:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 24802765HCID 24802765, compound

Product 1

HCID 58543938HCID 58543938, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 50 mg (0.11 mmol) of α-Chloromethyl-2,4-difluoro-3-methoxy-β-[(2-methylquinolin-5-yl)amino]-α-(trifluoromethyl)benzeneethanol in 4.9 dichloromethane at 0° C. are added 2.1 ml of a 1 M solution of boron tribromide in dichloromethane under argon. The reaction mixture is stirred for 16 hours in a temperature range of between 0° C. and 25° C. The reaction mixture is mixed at 0° C. with saturated sodium bicarbonate solution. After dilution with ethyl acetate the batch is allowed to come to room temperature, stirred for 10 minutes and extracted twice with ethyl acetate. The combined organic extracts are washed with saturated NaCl solution and dried over sodium sulfate. The solvent is partially evaporated and the remaining residue is passed through a short path of silica gel (ethyl acetate 100%). 43 mg of the desired compound are isolated.

Workup

  1. customto come to room temperature
  2. stirringstirred for 10 minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts are washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is partially evaporated

Sources & evidence

ORD record
ord-9dc450ba91bd41f7b86a5bc724d0d62c
Source dataset
uspto-grants-2012_05
Patent number
US08173676B2

Reaction notes

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