Dimethylacetamide → HCID 20784542, compound

HRID 549083Notes

Reaction equation

HRID 549083 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.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.Cl[Pd]Cl.[Fe+2]>[CH3:23][O:22][C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:24])[CH:12]=[C:11]2[C:9]1[NH:8][C:4]2=[N:5][CH:6]=[CH:7][C:2]([C:35]#[N:36])=[C:3]2[CH:10]=1)=[O:21]

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 86591420HCID 86591420, compound

Product 1

HCID 20784542HCID 20784542, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

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)ferrocenedichloropalladium (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-827f088d3f5c4a578b08f5b1f0ab846f
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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