Dimethylacetamide → HCID 68428506, compound

HRID 642563Notes

Reaction equation

HRID 642563 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]([CH3:19])([CH3:18])[CH3:17])[S:15][C:8]=2[C:7]=1[OH:20])=[O:5])[CH3:2].C[C:22]([N:24](C)C)=O>C(OCC)(=O)C.[Cl-].[NH4+].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-]#N.[Zn+2].[C-]#N>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:22]#[N:24])[C:9]2[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:15][C:8]=2[C:7]=1[OH:20])=[O:5])[CH3:2]

Participants

9

Reactant 2

HCID 31374DimethylacetamideHCID 86617377HCID 86617377, compound

Product 1

HCID 68428506HCID 68428506, compound

Reagents, catalysts & solvents 6

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 4-bromo-2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (100 mg, 0.28 mmol), tris(dibenzylideneacetone)dipalladium(0)(13 mg, 0.014 mmol), 1,1′-bis(diphenylphosphino) ferrocene (15 mg, 0.028 mmol), zinc dust (2 mg, 0.033 mmol), and zinc cyanide (20 mg, 0.168 mmol) in 0.56 mL of dimethylacetamide was heated at 115° C. for 5 h under a nitrogen atmosphere. The mixture was cooled, diluted with ethyl acetate and saturated aqueous ammonium chloride and filtered through a celite pad. The organic fraction was isolated and washed with brine, dried over anhydrous sodium sulfate, and concentrated to a crude residue. The crude material was purified by column chromatography, eluting the desired product from silica gel with a gradient of 10-60% ethyl acetate in hexanes to give 61 mg of the title compound. MS (ESI−): m/z 304.1 (M−1).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a celite pad
  3. customThe organic fraction was isolated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a crude residue
  7. customThe crude material was purified by column chromatography
  8. washeluting the desired product from silica gel with a gradient of 10-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-24ccb962a95e48e28eaddd5d4ae13928
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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