Ethyl Acetate → HCID 68428179, compound

HRID 642400Notes

Reaction equation

HRID 642400 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:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[S:15][C:8]=2[C:7]=1[OH:28])=[O:5])[CH3:2].C(OCC)(=O)C.[CH3:35][N:36](C)C(=O)C>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.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]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:35]#[N:36])[C:9]2[N:13]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[S:15][C:8]=2[C:7]=1[OH:28])=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 86617363HCID 86617363, compound

Product 1

HCID 68428179HCID 68428179, compound

Reagents, catalysts & solvents 4

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

Procedure

To a mixture of 2-(1-benzyl-1H-pyrazol-4-yl)-4-bromo-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (0.25 mg, 0.54 mmol), 1,1′-bis(diphenylphosphino)ferrocene (30.7 mg, 0.055 mmol), zinc dust (4.2 mg, 0.065 mmol), and zinc cyanide (38.3 mg, 0.33 mmol) in N,N-dimethylacetamide (1.11 mL) was added tris(dibenzylideneacetone)dipalladium(0)(24.9 mg, 0.027 mmol). The reaction mixture was heated at 120° C. for 5 h before ethyl acetate (70 mL) was added. The organic solution was washed with saturated ammonium chloride aqueous solution and saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 0.19 g of the title compound as a light yellow solid. MS: (+) m/z 406.3 (M+1).

Workup

  1. additionwas added
  2. washThe organic solution was washed with saturated ammonium chloride aqueous solution and saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-87206d64ed4c4d34b8c1cee7f6435793
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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