Acetic Acid → HCID 68386696, compound

HRID 1051173Notes

Reaction equation

HRID 1051173 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:5]=[C:4]([Br:18])[CH:3]=1.[F:19][C:20]([F:25])([F:24])[CH2:21][CH:22]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl.O>[Br:18][C:4]1[CH:3]=[C:2]([NH:1][CH2:22][CH2:21][C:20]([F:25])([F:24])[F:19])[C:10]2[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5049666Sodium triacetoxyborohydrideHCID 68386930HCID 68386930, compound

Product 1

HCID 68386696HCID 68386696, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-6-bromo-1H-benzimidazole-1-carboxylate (5.85 g, 18.74 mmol) in DCE (1000 mL) at rt was added 3,3,3-trifluoropropanal (6.30 g, 56.22 mmol, 3 eq), sodium triacetoxy borohydride (19.86 g, 93.70 mmol, 5 eq) and acetic acid (21.5 mL, 374.79 mmol, 20 eq) and the mixture was stirred for 2 h. Water and DCM was added, and the organic phase was separated and washed with water After addition of DCM (100 mL), the organic phase was washed with water and evaporated to yield 7.63 g tert-butyl 6-bromo-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazole-1-carboxylate (81.79%).

Workup

  1. customthe organic phase was separated
  2. washwashed with water
  3. additionAfter addition of DCM (100 mL)
  4. washthe organic phase was washed with water
  5. customevaporated

Sources & evidence

ORD record
ord-4250413464df4e65b85e7c949b0be1c4
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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