Methanol → HCID 21948899, compound

HRID 2182685Notes

Reaction equation

HRID 2182685 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:13]=[CH:14][C:15]([C:30]([F:33])([F:32])[F:31])([OH:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[O:27]C)([CH3:19])[CH3:18])[N:4]=1)[CH3:2].B(Br)(Br)Br.CO>ClCCl>[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:13][CH2:14][C:15]([C:30]([F:31])([F:32])[F:33])([OH:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[OH:27])([CH3:19])[CH3:18])[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 21948825HCID 21948825, compound

Product 1

HCID 21948899HCID 21948899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

230 mg (0.49 mmol) of 1-(2-ethylquinolin-5-ylimino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 4.5 ml of dichloromethane is mixed at 0° C. with 7.30 ml (7.30 mmol) of a 1 M boron tribromide solution. After 23 hours at room temperature, the reaction is brought to a halt by the addition of 30 ml of methanol. The reaction mixture is allowed to stir for one hour at room temperature, and then the solvent is removed in a vacuum. After chromatography on silica gel with ethyl acetate-methanol (0-10%), 60 mg (27% of theory) of the product is obtained.

Workup

  1. customthe solvent is removed in a vacuum
  2. customAfter chromatography on silica gel with ethyl acetate-methanol (0-10%), 60 mg (27% of theory) of the product is obtained

Sources & evidence

ORD record
ord-c945fad9fb84414fb8a5515813975c4d
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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