Dimethylformamide → HCID 178510114, compound

HRID 400718Notes

Reaction equation

HRID 400718 reaction equation
Br[C:2]1[CH:10]=[C:9]([F:11])[C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.[CH3:12][N:13](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].[Zn].C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[F:11][C:9]1[C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=[C:2]([C:12]#[N:13])[CH:10]=1

Participants

8

Reactant 2

HCID 6228DimethylformamideHCID 178505413HCID 178505413, compound

Product 1

HCID 178510114HCID 178510114, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11192Zinc AcetateCatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of 5-bromo-7-fluoro-1H-benzimidazole obtained from step 1 (2.50 g; 11.63 mmol), zinc cyanide (Adrich, 819 mg; 6.98 mmol), tris(dibenzylideneacetone)dipalladium (Adrich, 319 mg; 0.35 mmol), 1,1-bis(diphenylphosphino)ferrocene (483 mg; 0.87 mmol), zinc (Adrich, 30 mg; 0.47 mmol) and zinc acetate (Adrich, 85 mg; 0.47 mmol) in dry DMF (25 mL) under inert atmosphere was heated at 120° C. for 16 hours. Reaction mixture was filtered over a pad of celite washed with EtOAc. The organics were washed with water, dried over MgSO4 and evaporated under vacuum to afford a brown solid that was triturated with EtOH and filtered to give the title compound as a brown solid 1H NMR (DMSO-d6) δ 13.40 (bs, 1H), 8.55 (s, 1H), 8.04 (s, 1H), 7.51-7.48 (d, J=10.7 Hz, 1H). LC/MS (Method B): 162.1 (M+H)+.

Workup

  1. customReaction mixture
  2. filtrationwas filtered over a pad of celite
  3. washwashed with EtOAc
  4. washThe organics were washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customto afford a brown solid that
  8. customwas triturated with EtOH
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2a9c7cd2c1234fe88a6ba7713af0a563
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…