Boron tribromide → HCID 46944855, compound

HRID 2388305Notes

Reaction equation

HRID 2388305 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:18][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)=[O:21])[CH2:16]2)[CH2:11][CH2:10]1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:10][CH2:11][CH:12]([N:15]2[CH2:18][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)=[O:21])[CH2:16]2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 46944854HCID 46944854, compound

Product 1

HCID 46944855HCID 46944855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-({1-[4-(3-Methoxy-pyridin-4-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (0.101 g, 0.206 mmol, as prepared in Example 8) was dissolved in anhydrous dichloromethane (10 mL) under Ar, treated with 0.83 N boron tribromide in dichloromethane (Aldrich, 2.00 mL, 1.66 mmol), and stirred at ambient temperature for 24 h. After quenching with saturated aqueous NaHCO3, the reaction was stirred at ambient temperature for 30 mins and extracted thrice with 3:1 EtOAc/2-propanol. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo giving a gold gum that was purified by preparative thin layer chromatography on silica gel (15% MeOH in CH2Cl2, 0.6N in ammonia), giving the title compound as a pale yellow solid.

Workup

  1. customAfter quenching with saturated aqueous NaHCO3
  2. stirringthe reaction was stirred at ambient temperature for 30 mins
  3. extractionextracted thrice with 3:1 EtOAc/2-propanol
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customgiving a gold gum that
  9. customwas purified by preparative thin layer chromatography on silica gel (15% MeOH in CH2Cl2, 0.6N in ammonia)

Sources & evidence

ORD record
ord-7d501d83c503404cb81c3edf2d82cddc
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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