Ammonium formate → HCID 86757539, compound

HRID 382475Notes

Reaction equation

HRID 382475 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:17][C@H:18]([N:20]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][C:39]([F:42])([F:41])[F:40])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)(=[O:3])[NH2:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([CH2:17][C@H:18]([N:20]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][C:39]([F:40])([F:41])[F:42])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])[CH3:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9]2)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 25152558HCID 25152558, compound

Product 1

HCID 86757539HCID 86757539, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-2,3-dihydro-1H-indol-5-yl]-1-methylethyl]-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]carbamate (12.0 g) and ammonium formate (12.7 g) were dissolved in methanol (300 ml), and 10% palladium on carbon (1.20 g) was carefully added to the solution. The mixture was heated overnight under reflux, and the solvent was removed in vacuo. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give amorphous tert-butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]carbamate (12.2 g).

Workup

  1. temperatureThe mixture was heated overnight
  2. temperatureunder reflux
  3. customthe solvent was removed in vacuo
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-900228ac13d74e30975ae412cb672289
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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