Boron tribromide → HCID 70937174, compound

HRID 1875235Notes

Reaction equation

HRID 1875235 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[N:7]=[C:8]([O:33]C)[NH:9][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[C:25]([Cl:31])[CH:24]=2)[C:16]=1[F:32])=[O:12]>C(Cl)Cl>[Cl:5][C:6]1[NH:7][C:8](=[O:33])[NH:9][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[C:25]([Cl:31])[CH:24]=2)[C:16]=1[F:32])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 178494205HCID 178494205, compound

Product 1

HCID 70937174HCID 70937174, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

BBr3 (0.28 mL of a 1M solution in CH2Cl2, 0.28 mmol) was added to a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(methyloxy)-1H-imidazole-5-carboxamide (0.044 g, 0.093 mmol) in CH2Cl2 (1 mL). After 2 h, additional BBr3 (0.30 mL of a 1M solution in CH2Cl2, 0.30 mmol) was added and the reaction mixture was stirred for 3 days. The solution was evaporated, additional BBr3 (1 mL of a 1M solution in CH2Cl2, 1 mmol) was added and the reaction mixture was stirred for 5 days. Sat'd NaHCO3 was added and the mixture was extracted with EtOAc and then CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) to provide the title compound (0.006 g, 15%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.38 (s, 1H) 10.41 (s, 1H) 8.06 (t, J=5.68 Hz, 1H) 7.82 (s, 1H) 7.48-7.54 (m, 2H) 7.46 (t, J=1.97 Hz, 1

Workup

  1. customThe solution was evaporated
  2. additionadditional BBr3 (1 mL of a 1M solution in CH2Cl2, 1 mmol) was added
  3. stirringthe reaction mixture was stirred for 5 days
  4. additionSat'd NaHCO3 was added
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. custompurified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-40b5a36dc19b4190b4abe2f7fa6e9617
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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