Borane → HCID 20098380, compound

HRID 1768998Notes

Reaction equation

HRID 1768998 reaction equation
B.[Na].[C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:25]C(=O)C)=[C:11]([CH:24]=1)[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2)=[O:13])(=[O:5])[CH3:4]>CO>[C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([OH:25])=[C:11]([CH:24]=1)[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2)=[O:13])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 6331BoraneHCID 5360545SodiumHCID 20098370HCID 20098370, compound

Product 1

HCID 20098380HCID 20098380, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g of boron hydride and sodium were added to a suspension of 1.5 g of the product of Step B in 150 ml of methanol and the mixture was refluxed for 2 hours. The methanol was partially removed under reduced pressure at 50° C. and the mixture was diluted with 200 ml of water and 200 ml of ethyl acetate. The mixture was extracted with ethyl acetate and the extracts were dried and evaporated to dryness under reduced pressure at 50° C. to obtain 1.35 g of 5-acetylamino-2-hydroxy-N-(1H-indol-4-yl)-benzamide which was used as is for the next step.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe methanol was partially removed under reduced pressure at 50° C.
  3. additionthe mixture was diluted with 200 ml of water and 200 ml of ethyl acetate
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe extracts were dried
  6. customevaporated to dryness under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-efc0e568ffee4d86be643d14a9cba1d1
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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