Boron tribromide → 3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol

HRID 1875726Notes

Reaction equation

HRID 1875726 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:18])[C:15]([F:17])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]2[C:20]([O:25]CC3C=CC(OC)=CC=3)=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:18])[C:15]([F:17])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]2[C:20]([OH:25])=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67049968HCID 67049968, compound

Product 1

HCID 1785177063-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-olYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-cyclohexylmethyl-5,6-difluoro-2-[2-(4-methoxy-benzyloxy)-pyridin-3-yl]-1H-benzoimidazole (2.32 g, 5 mmol) in dichloromethane (40 ml) was added boron tri bromide (1M solution in dichloromethane; 21 ml, 21 mmol) at 25° C., and the resulting mixture was allowed to stir for 16 h at the same temperature. The reaction mixture was then quenched with saturated aqueous solution of sodium bi carbonate solution, further diluted with dichloromethane (30 ml). Organic layer was washed with water, and then with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to afford the crude material. Crude product was purified by column chromatography using silica gel (5-10% ethyl acetate/n-hexane) to give the title compound as a colorless solid (39%). MS (Turbo Spray): m/z=344.3 (M+H).

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bi carbonate solution
  2. additionfurther diluted with dichloromethane (30 ml)
  3. washOrganic layer was washed with water
  4. dry with materialwith brine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto afford the crude material
  8. customCrude product was purified by column chromatography

Sources & evidence

ORD record
ord-7babd16e09c24ea698791de094e671be
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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