Dimethylacetamide → HCID 22031942, compound

HRID 1792590Notes

Reaction equation

HRID 1792590 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:39]([C:42]3[S:43][CH:44]=[CH:45][N:46]=3)=[CH:40][N:41]=2)[CH:5]=[C:6]([C:8]2[C:9]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[N:10][N:11]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH:7]=1.[CH3:47][N:48](C)C(=O)C>O.C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Zn].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([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:9]2[C:8]([C:6]3[CH:7]=[C:2]([C:47]#[N:48])[C:3]4[N:4]([C:39]([C:42]5[S:43][CH:44]=[CH:45][N:46]=5)=[CH:40][N:41]=4)[CH:5]=3)=[CH:12][N:11]([C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=2)=[CH:37][CH:36]=1

Participants

9

Reactant 2

HCID 31374DimethylacetamideHCID 22031593HCID 22031593, compound

Product 1

HCID 22031942HCID 22031942, compound

Reagents, catalysts & solvents 6

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 213 mg 2-{8-chloro-6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}-1,3-thiazole obtained in Example 404 in 2 mL N,N-dimethylacetamide, together with 24 mg zinc cyanide, 6 mg zinc powder, 12 mg tris(dibenzylidene acetone)dipalladium (0) and 15 mg diphenylphosphinoferrocene, was heated at 150° C. for 5 hours, and the reagents were added in the same amounts as described above, and the mixture was heated at 150° C. for 10 hours. The reaction solution was diluted with water and ethyl acetate and filtered through Celite, and the organic layer was washed with brine. The solution was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) and then recrystallized to give 68 mg of the title compound (yellow solid).

Workup

  1. additionthe reagents were added in the same amounts
  2. filtrationfiltered through Celite
  3. washthe organic layer was washed with brine
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customrecrystallized

Sources & evidence

ORD record
ord-867b0a31188c4f479c781a6d85d46632
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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