Boron tribromide → HCID 76284755, compound

HRID 1480182Notes

Reaction equation

HRID 1480182 reaction equation
[CH:1]1([C:4]2[C:5]([O:30][CH2:31][C:32]([F:35])([F:34])[F:33])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:24]3[N:28]=[C:27]([CH3:29])[O:26][N:25]=3)([CH3:23])[CH2:14][O:15]CC3C=CC=CC=3)=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([C:4]2[C:5]([O:30][CH2:31][C:32]([F:33])([F:35])[F:34])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:24]3[N:28]=[C:27]([CH3:29])[O:26][N:25]=3)([CH3:23])[CH2:14][OH:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90204028HCID 90204028, compound

Product 1

HCID 76284755HCID 76284755, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-cyclopropyl-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-phenylmethoxypropan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide (example 112e, 570 mg, 1.16 mmol) in dry dichloromethane (6 ml) cooled down to 0° C. under an argon atmosphere was added a 1.0M solution of boron tribromide in dichloromethane (1.28 ml, 1.28 mmol). The reaction mixture was stirred at 0° C. for 15 minutes followed by stirring at room temperature for 1 hour. The reaction was diluted with dichloromethane, quenched by addition of a 2M aqueous solution of sodium carbonate and the bi-phasic mixture was stirred for 10 minutes. The bi-phasic mixture was poured into a separatory funnel and extracted. The organic phase was collected and the aqueous phase was back-extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (394 mg, 85%). MS (ESI, m/z): 401.6 (M+H+).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customquenched by addition of a 2M aqueous solution of sodium carbonate
  3. stirringthe bi-phasic mixture was stirred for 10 minutes
  4. additionThe bi-phasic mixture was poured into a separatory funnel
  5. extractionextracted
  6. customThe organic phase was collected
  7. extractionthe aqueous phase was back-extracted with dichloromethane
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. customevaporated down to dryness
  10. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-bf394b57e2b045d4bce4d629fc1f779c
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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