Ammonium formate → HCID 57473934, compound

HRID 1868427Notes

Reaction equation

HRID 1868427 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:18][CH:19]([NH:24][S:25]([C:28]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=1[CH3:36])(=[O:27])=[O:26])[C:20]([F:23])([F:22])[F:21])=[CH:12][NH:13]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:34][C:33]1[CH:32]=[C:31]([CH3:35])[CH:30]=[C:29]([CH3:36])[C:28]=1[S:25]([NH:24][CH:19]([CH2:18][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[OH:8])[NH:13][CH:12]=1)[C:20]([F:23])([F:21])[F:22])(=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11684972HCID 11684972, compound

Product 1

HCID 57473934HCID 57473934, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred solution of 80 mg (0.15 mmol) of N-[1-(4-benzyloxy-1H-indol-3-ylmethyl)-2,2,2-trifluoroethyl]-2,4,6-trimethylbenzenesulfonamide in 5 mL of methanol was added 20 mg of 10% palladium on carbon followed by 48.7 mg (0.77 mmol) of ammonium formate. The reaction mixture stirred at room temperature for 1 hour and was then diluted with methanol, filtered through CELITE® filter aid, and concentrated in vacuo. The residue was diluted with cold water and the precipitate was filtered, washed with water, and dried to afford a white solid which was purified by preparative TLC eluting with ethyl acetate-hexanes (4:6) to afford 30 mg (45%) of the title compound as an off-white solid.

Workup

  1. filtrationfiltered through CELITE®
  2. filtrationfilter aid
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with cold water
  5. filtrationthe precipitate was filtered
  6. washwashed with water
  7. customdried
  8. customto afford a white solid which
  9. customwas purified by preparative TLC
  10. washeluting with ethyl acetate-hexanes (4:6)

Sources & evidence

ORD record
ord-e5eb8f942fd740fc92dda98c174114e1
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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