Ethyl Acetate → HCID 68428125, compound

HRID 642407Notes

Reaction equation

HRID 642407 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([Cl:16])=[C:14]([Cl:17])[N:13]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].C(OCC)(=O)C.[CH3:30][N:31](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[C:7]([OH:23])=[C:8]2[C:15]([Cl:16])=[C:14]([Cl:17])[N:13]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:9]2=[C:10]([C:30]#[N:31])[N:11]=1)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 86617364HCID 86617364, compound

Product 1

HCID 68428125HCID 68428125, 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 7-bromo-2,3-dichloro-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (1.16 g, 2.74 mmol), 1,1′-bis(diphenylphosphino)ferrocene (228 mg, 0.411 mmol), zinc dust (32.1 mg, 0.493 mmol), and zinc cyanide (290 mg, 2.47 mmol) in N,N-dimethylacetamide (8.7 mL) was added tris(dibenzylideneacetone)dipalladium(0)(188 mg, 0.21 mmol). The reaction mixture was heated at 120° C. for 1.5 hours before ethyl acetate (100 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 0-30% ethyl acetate in hexanes to produce 0.65 g of the title compound as a light yellow solid. MS: (+) m/z 370.2 (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 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7dbc4125b9e941689ba0d871932f2580
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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