Ammonium formate → HCID 9845791, compound

HRID 275356Notes

Reaction equation

HRID 275356 reaction equation
C([O-])=O.[NH4+].[CH3:5][C:6]1[N:7]([C:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][NH:33][C:32]3=[O:36])[CH2:27][CH:28]=2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[CH:12][C:11]([CH3:22])=[CH:10][CH:9]=2>[Pd].C(O)C>[CH3:5][C:6]1[N:7]([CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][NH:33][C:32]3=[O:36])[CH2:27][CH2:28]2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)=[CH:12][C:11]([CH3:22])=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10048445HCID 10048445, compound

Product 1

HCID 9845791HCID 9845791, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (12 g) was added in small portions during 18 h to a refluxing mixture of 2,5-dimethyl-3-(4-fluorophenyl)-1-[1-[2-(imidazolidin-2-on-1-yl)ethyl]1,2,3,6-tetrahydropyridin-4-yl]-1H-indole 6a (1.9 g), 5% palladium on activated carbon (1 g) and ethanol (50 ml). The reaction mixture was cooled to room temperature and the solvents were evaporated in vacuo. After addition of water the mixture was made alkaline with concentrated NaOH and extracted with ethyl acetate (2×50 ml).The combined organic phases were dried (Na2SO4) and the solvents were evaporated in vacuo. This afforded the title compound which crystallized from diethyl ether. Yield 0.2 g, mp 188°-190° C.

Workup

  1. customthe solvents were evaporated in vacuo
  2. additionAfter addition of water the mixture
  3. extractionextracted with ethyl acetate (2×50 ml).The combined organic phases
  4. dry with materialwere dried (Na2SO4)
  5. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-bc0c7c51ae6546db88b78b718e155389
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

Loading…