Dimethylacetamide → HCID 20784542, compound

HRID 2182254Notes

Reaction equation

HRID 2182254 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=4)[N:13]([CH3:24])[CH:12]=3)=[CH:10][C:3]=12.[CH3:35][N:36](C)C(=O)C>[Zn].[C-]#N.[Zn+2].[C-]#N>[C:35]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=4)[N:13]([CH3:24])[CH:12]=3)=[CH:10][C:3]=12)#[N:36]

Participants

5

Reactant 2

HCID 31374DimethylacetamideHCID 86591420HCID 86591420, compound

Product 1

HCID 20784542HCID 20784542, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid, methyl ester [0.4 g, Reference Example 2(r)], zinc powder (0.05 g), zinc cyanide (0.117 g), [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichlroromethane (catalytic) and N,N-dimethylacetamide (8 mL) was heated at 130-150° C. for 5 hours. The reaction mixture was cooled, filtered and the precipitated washed with dimethylformamide (2 mL). The filtrate was diluted with ethyl acetate (120 mL) and the solution extracted with water (2×20 mL). The combined organic layer was evaporated and the residue subjected to flash column chromatography on silica gel eluting with a mixture of heptane and ethyl acetate (7:3 v/v) moving to neat ethyl acetate to give the title compound (0.12 g) as a bright yellow solid. MS: 331(MH+). HPLC(Method C): RT=4.01 minutes.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe precipitated washed with dimethylformamide (2 mL)
  4. additionThe filtrate was diluted with ethyl acetate (120 mL)
  5. extractionthe solution extracted with water (2×20 mL)
  6. customThe combined organic layer was evaporated
  7. additionthe residue subjected to flash column chromatography on silica gel eluting with a mixture of heptane and ethyl acetate (7:3 v/v)

Sources & evidence

ORD record
ord-daeca5e1bd0845279264e5c893db3308
Source dataset
uspto-grants-2005_05
Patent number
US06897207B2

Reaction notes

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