Dimethylacetamide → HCID 68428589, compound

HRID 642371Notes

Reaction equation

HRID 642371 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:24])=[O:5])[CH3:2].C[C:26]([N:28](C)C)=O>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].[C-]#N.[Zn+2].[C-]#N.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:26]#[N:28])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:24])=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 86617358HCID 86617358, compound

Product 1

HCID 68428589HCID 68428589, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-7-hydroxy-2-(3-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (197 mg, 0.48 mmole), tris(dibenzylideneacetone)-dipalladium(0)(22 mg, 0.02 mmole), 1,1′-bis(diphenylphosphino)ferrocene (27 mg, 0.04 mmole), zinc cyanide (27 mg, 0.29 mmole) and zinc (4 mg, 0.06 mmole) in dimethylacetamide (968 μl) was stirred at 120° C. for 4.5 h before it was cooled to room temperature, partitioned between ethyl acetate and water, filtered. The filtrate washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a yellow solid (32 mg). MS: (+) m/z 356.24 (M+1), MS: (−) m/z 354.24 (M−1).

Workup

  1. temperaturewas cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. filtrationfiltered
  4. washThe filtrate washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane

Sources & evidence

ORD record
ord-7ee870955e864f20928c1172c1937f8b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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