Sodium Bicarbonate → HCID 17958793, compound

HRID 351932Notes

Reaction equation

HRID 351932 reaction equation
FC(F)(F)C([O-])=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:20]2[C:28]3[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][N:33]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][NH+:42]=4)CC4C=CC=CC=4)=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>CC(C)=O.[Pd]>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:20]2[C:28]3[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][NH:33][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=4)=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 69869710HCID 69869710, compound

Product 1

HCID 17958793HCID 17958793, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

60 mg (94 μmol) of 26 are dissolved in 5 ml of acetone and hydrogenated for 10 hours at RT and atmospheric pressure in the presence of 40 mg (0.48 mmol) of sodium hydrogen carbonate and 20 mg of palladium/activated carbon (10%). Removal of the catalyst by filtration and evaporation of the solution gives 3-(4-fluorophenyl)-3-{6-[3-(pyridin-2-ylamino)propoxy]indol-3-yl}propionic acid. Preparative HPLC on RP-18 gives 3-(4-fluorophenyl)-3-{6-[3-(pyridin-2-ylamino)propoxy]indol-3-yl}propionic acid trifluoroacetate.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the solution

Sources & evidence

ORD record
ord-b76e5b82239340659401cbb7d884af48
Source dataset
uspto-grants-2004_06
Patent number
US06743810B2

Reaction notes

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