Boron tribromide → Ammonia

HRID 2387693Notes

Reaction equation

HRID 2387693 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:37]([O:38]C)=[CH:36][CH:35]=[CH:34][C:7]=1[O:8][CH:9]1[CH2:12][N:11]([C:13]([CH3:33])([CH3:32])[CH2:14][CH2:15][C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([NH2:19])=[O:18])[CH2:10]1>ClCCl>[NH3:11].[F:5][C:6]1[C:37]([OH:38])=[CH:36][CH:35]=[CH:34][C:7]=1[O:8][CH:9]1[CH2:12][N:11]([C:13]([CH3:33])([CH3:32])[CH2:14][CH2:15][C:16]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([NH2:19])=[O:18])[CH2:10]1

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 59423896HCID 59423896, compound

Product 2

HCID 222AmmoniaHCID 16065407HCID 16065407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (1M in dichloromethane, 1.5 mL, 1.5 mmol) was added to an ice-cooled solution of the product of example 133 (45 mg, 0.094 mmol) in dichloromethane (5 mL) and the mixture was stirred at 0° C. for 45 minutes. The reaction was warmed to room temperature. After 15 min, a further 1.5 mL boron tribromide was added. After 20 minutes, the reaction was quenched with 0.88 ammonia (20 mL) and the solution stirred at room temperature for 18 hours. The organic layer was separated and washed with saturated sodium hydrogen carbonate solution (10 mL) and dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia 100:0:0 to 98:2:0.2 to give the title compound in 100% yield (44 mg).

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. waitAfter 15 min
  3. waitAfter 20 minutes
  4. customthe reaction was quenched with 0.88 ammonia (20 mL)
  5. stirringthe solution stirred at room temperature for 18 hours
  6. customThe organic layer was separated
  7. washwashed with saturated sodium hydrogen carbonate solution (10 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by column chromatography on silica gel
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ac9cd69cfa65443fb9868f18e9eafb69
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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