Sodium Formate → HCID 22467241, compound

HRID 369346Notes

Reaction equation

HRID 369346 reaction equation
[C]=O.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:26]3[C:34]4[C:29](=[CH:30][C:31](Br)=[CH:32][CH:33]=4)[N:28]([CH3:36])[CH:27]=3)[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1.[CH:37]([O-])=[O:38].[Na+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH:37]=[O:38])=[CH:32][CH:33]=4)[N:28]([CH3:36])[CH:27]=3)[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[O:14])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

6

Reactant 3

HCID 2723810Sodium FormateHCID 22467232HCID 22467232, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 22467241HCID 22467241, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Carbon monoxide was bubbled through a stirred solution of 3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-6-bromo-1-methyl-1H-indole (from Example 55, 400 mg, 0.79 mmol), sodium formate (107 mg, 1.57 mmol) and dichlorobis(triphenylphosphine)-palladium (II) (11 mg, 0.016 mmol) in dimethylformamide (6 ml) at 110° C. for 4 h. The reaction mixture was cooled and extracted from 1N hydrochloric acid with ethyl acetate (2×50 ml). The organic layers were dried (MgSO4) and concentrated. Flash column chromatography (elution with 95% dichloromethane/5% methanol) gave the product (320 mg) as a fawn solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted from 1N hydrochloric acid with ethyl acetate (2×50 ml)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. washFlash column chromatography (elution with 95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-b5ad88723dc74609ab81a2c2b026e5b1
Source dataset
uspto-grants-2000_10
Patent number
US06136843

Reaction notes

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