Boron tribromide → HCID 178481999, compound

HRID 1518052Notes

Reaction equation

HRID 1518052 reaction equation
C([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]2[C:31]([CH2:32][N:33]([C:49]3[N:50]=[N:51][N:52]([CH3:54])[N:53]=3)[CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=3)=[CH:30][C:29]3[C:24](=[CH:25][C:26]([F:56])=[C:27]([F:55])[CH:28]=3)[N:23]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[F:43][C:41]([F:42])([F:44])[C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([C:45]([F:46])([F:47])[F:48])[CH:38]=1)[CH2:34][N:33]([CH2:32][C:31]1[C:22]([N:18]2[CH2:19][CH2:20][CH2:21][C@@H:17]2[C@H:14]2[CH2:13][CH2:12][C@H:11]([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15]2)=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([F:55])=[C:26]([F:56])[CH:25]=2)[C:49]1[N:50]=[N:51][N:52]([CH3:54])[N:53]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178482000HCID 178482000, compound

Product 1

HCID 178481999HCID 178481999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-N-[2-((R)-2-{4-[2-(benzyloxy)ethyl]cyclohexyl}pyrrolidin-1-yl)-6,7-difluoroquinolin-3-ylmethyl]-N-[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amine (11.0 g, 14.0 mmol) in CH2Cl2 (120 mL) is added dropwise BBr3 (1.0 M CH2Cl2 solution, 18.0 mL, 18.0 mmol) at 0° C. and stirred at room temperature for 10 min. The reaction mixture is quenched by addition of sat. NaHCO3 aq. extracted with ethyl acetate, and the organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give trans-2-(4-{(R)-1-[3-({[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexyl)ethanol.

Workup

  1. customThe reaction mixture is quenched by addition of sat. NaHCO3 aq.
  2. extractionextracted with ethyl acetate
  3. washthe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54e4efa88176426396f9ed1adb4a3ab3
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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