Dimethylformamide → HCID 67241608, compound

HRID 642767Notes

Reaction equation

HRID 642767 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)N(C)[C:10]1[C:9]3[CH:16]=C[CH:18]=[CH:19][C:8]=3[S:7][CH2:6][C:5]2=1.[C:20]([Cu])#[N:21].[CH3:23][N:24]([CH:26]=O)C>>[CH3:16][CH:9]1[C:10]2[C:23]3[N:24]=[CH:26][CH:18]=[CH:19][C:8]=3[S:7][CH2:6][C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([C:20]#[N:21])[CH:3]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 44411761HCID 44411761, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67241608HCID 67241608, compound

Conditions

Temperature
170 °C

Procedure

A mixture of 8-bromo-11-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (270 mg), as prepared in Example 57, and CuCN (270 mg) in DMF (25 ml) was reflux overnight at 170° C. The reaction mixture was filtered through a pad of Celite and then partitioned between saturated NaHCO3 aqueous solution and EtOAc. The aqueous layer was extracted with EtOAc, the organic layers were dried and concentrated to yield crude product. The crude product was purified by chromatography (Hexane:ethyl acetate=5:1) to yield the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. custompartitioned between saturated NaHCO3 aqueous solution and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. customthe organic layers were dried
  5. concentrationconcentrated
  6. customto yield crude product
  7. customThe crude product was purified by chromatography (Hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-091652d8e5f94fd187ff853f0c8c0dd3
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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