Dimethylformamide → HCID 178426390, compound

HRID 400721Notes

Reaction equation

HRID 400721 reaction equation
Br[C:2]1[CH:10]=[C:9]([CH3:11])[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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH3:11][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 178422430HCID 178422430, compound

Product 1

HCID 178426390HCID 178426390, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11192Zinc AcetateCatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of 5-bromo-7-methyl-1H-benzimidazole obtained in step 1 (2.80 g; 13.27 mmol), zinc cyanide (934 mg; 7.96 mmol), tris(dibenzylideneacetone)dipalladium (364 mg; 0.40 mmol), 1,1′-bis(diphenylphosphino)ferrocene (551 mg; 0.99 mmol), zinc (34 mg; 0.53 mmol) and zinc acetate (97 mg; 0.53 mmol) in dry DMF (28 mL) under inert atmosphere was heated at 120° C. for 16 hours. Reaction mixture was filtered over a pad of celite and 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, filtered to give the title compound as a beige solid. 1H NMR (DMSO-d6) δ 13.11 (br s, 1H), 8.45 (s, 1H), 8.02-7.90 (m, 1H), 7.42 (m, 1H), 2.54 (m, 3H). LC/MS (Method B): 158.2 (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-2f58324ed16d42539bdf7e44528008dc
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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