Boron tribromide → HCID 136272168, compound

HRID 1747234Notes

Reaction equation

HRID 1747234 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:32]=[CH:31][C:10]([CH2:11][C@@H:12]2[CH2:17][O:16][CH2:15][CH2:14][N:13]2[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[N:30]=[CH:29][CH:28]=[N:27]2)=[O:19])=[CH:9][C:8]=1[C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1>C(Cl)Cl>[OH:6][C:7]1[CH:32]=[CH:31][C:10]([CH2:11][C@@H:12]2[CH2:17][O:16][CH2:15][CH2:14][N:13]2[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[N:30]=[CH:29][CH:28]=[N:27]2)=[O:19])=[CH:9][C:8]=1[C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71565871HCID 71565871, compound

Product 1

HCID 136272168HCID 136272168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide 1M soln. in DCM (0.8 mL, 0.8 mmol) was added to a −78° C. solution of [(R)-3-(4-methoxy-3-pyrimidin-2-yl-benzyl)-morpholin-4-yl]-(2-[1,2,3]triazol-2-yl-phenyl)-methanone Example 5 (72 mg, 0.16 mmol) in DCM (5 mL) and after complete addition the the reaction mixture was warmed to RT and stirred for 6 h. The reaction was quenched with sat. aq. NaHCO3 and the layers were separated. The aqueous layer was extracted with DCM (2×) and the combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by prep. HPLC (method F) to give the title compound as a white solid. LC-MS D: tR=0.80 min; [M+H]+=443.03.

Workup

  1. additionafter complete addition the the reaction mixture
  2. customThe reaction was quenched with sat. aq. NaHCO3
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with DCM (2×)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-6971264ca0d14c6799b9b7d5cf5d862f
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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