Triethylamine → HCID 58493979, compound

HRID 2360495Notes

Reaction equation

HRID 2360495 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3Br)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C]=O.[C:41]([O:44][CH2:45]C)(=[O:43])C>CO.CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[C:41]([O:44][CH3:45])=[O:43])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 58493992HCID 58493992, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 58493979HCID 58493979, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Argon is piped for 10 minutes through a suspension of 18.8 g 7-bromo-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide in 250 ml of methanol and 50 ml N,N-dimethylformamide. Then 7.2 ml triethylamine and 2.3 g [1,1′-bis(diphenylphosphino)ferrocene]-palladium-II-dichloride-dichloromethane complex are added and 2 bar of carbon monoxide are compressed in for 15 hours at 80° C. Then the solvents are eliminated in vacuo, the residue is taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvent is eliminated in vacuo and the residue is extracted from methanol. The solid is suction filtered, washed with a little methanol and dried.

Workup

  1. customare compressed in for 15 hours at 80° C
  2. washwashed with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialAfter drying with magnesium sulphate the solvent
  4. extractionthe residue is extracted from methanol
  5. filtrationfiltered
  6. washwashed with a little methanol
  7. customdried

Sources & evidence

ORD record
ord-f49e1febccee487a8394a254a0cdce1c
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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