Dimethylformamide → HCID 16731188, compound

HRID 549487Notes

Reaction equation

HRID 549487 reaction equation
[Cu]([C:4]#[N:5])C#N.[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:23]3[N:22]=[C:21]([C:24]4[C:29](Br)=[CH:28][CH:27]=[CH:26][C:25]=4Br)[NH:20][C:19]=3[C:18]3[C:13](=[CH:14][C:15]([C:32]([OH:35])([CH3:34])[CH3:33])=[CH:16][CH:17]=3)[C:11]=2[CH:12]=1.[NH4+].[OH-].C(OCC)(=O)C.[CH3:44][N:45](C=O)C>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:23]3[N:22]=[C:21]([C:24]4[C:25]([C:4]#[N:5])=[CH:26][CH:27]=[CH:28][C:29]=4[C:44]#[N:45])[NH:20][C:19]=3[C:18]3[C:13](=[CH:14][C:15]([C:32]([OH:35])([CH3:33])[CH3:34])=[CH:16][CH:17]=3)[C:11]=2[CH:12]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 86614871HCID 86614871, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 16731188HCID 16731188, compoundYield 25%

Conditions

Temperature
80 °C

Procedure

Copper cyanide (420 mg, 4.7 mmol) was added to a room temperature solution of 2-[6-bromo-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazol-9-yl]propan-2-ol from Step 4 (1.25 g, 2.1 mmol) in DMF (100 mL) and the mixture heated at 80° C. for 18 h, after which it was poured into a mixture of NH4OH and ethyl acetate and stirred for 1 h. The aqueous phase was extracted with ethyl acetate, the organic layer washed once with water, once with brine, dried over Na2SO4, filtered and concentrated. The material obtained after purification by flash chromatography on silica (20-80% ethyl acetate in toluene) was swished in ethyl acetate and THF for 2 h and then filtered to afford 2-[6-bromo-9-(1-hydroxy-1-methylethyl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile as a yellow solid (250 mg, 25%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe organic layer washed once with water, once with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material obtained
  7. customafter purification by flash chromatography on silica (20-80% ethyl acetate in toluene)
  8. waitTHF for 2 h
  9. filtrationfiltered

Sources & evidence

ORD record
ord-36b2be7a1b254ac3b71296664797caa7
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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