Ethyl Acetate → HCID 71061894, compound

HRID 2201870Notes

Reaction equation

HRID 2201870 reaction equation
Br[C:2]1[CH:29]=[C:28]([Cl:30])[C:5]([C:6]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([N:17]([C:23]([CH:25]4[CH2:27][CH2:26]4)=[O:24])[C:18]([CH:20]4[CH2:22][CH2:21]4)=[O:19])[C:11]=3[CH:10]=[CH:9]2)=[O:7])=[C:4]([Cl:31])[CH:3]=1.[Cu]([C:35]#[N:36])[C:33]#[N:34].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH:20]1([C:18]([N:17]([C:12]2[C:11]3[CH:10]=[CH:9][N:8]([C:6](=[O:7])[C:5]4[C:28]([Cl:30])=[CH:29][C:2]([C:33]#[N:34])=[CH:3][C:4]=4[Cl:31])[C:16]=3[CH:15]=[CH:14][N:13]=2)[C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])=[O:19])[CH2:22][CH2:21]1.[Cl:30][C:28]1[CH:29]=[C:2]([C:35]#[N:36])[CH:3]=[C:4]([Cl:31])[C:5]=1[C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:17][C:18]([CH:20]3[CH2:21][CH2:22]3)=[O:19])[C:11]=2[CH:10]=[CH:9]1)=[O:7]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 71061873HCID 71061873, compoundHCID 178418260HCID 178418260, compound

Product 2

HCID 71061894HCID 71061894, compoundHCID 71618553HCID 71618553, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-[1-(4-bromo-2,6-dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]-N-(cyclopropylcarbonyl)cyclopropanecarboxamide (40 mg, 0.11 mmol), dppf (10 mg, 0.018 mmol), copper cyanide (41 mg, 0.45 mmol) and cesium carbonate (110 mg, 0.33 mmol) in 1,4-dioxane (2 mL) was heated in a sealed vial at 90° C. for 4 hours. Ethyl acetate was added and washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulphate and concentrated to get the crude residue which was purified by silica gel column chromatography to afford N-(cyclopropylcarbonyl)-N-[1-(2,6-dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide and N-[1-(2,6-dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated
  4. customto get the crude residue which
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-330be62508a24d23bcc23efe1697238a
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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