1,1-dimethylethyl 4-[4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate → 1,1-dimethylethyl 4-[4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 1180884Notes

Reaction equation

HRID 1180884 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:15]([C:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=4)=[CH:16][C:9]=23)[C:5]([C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=2)=[N:4]1)[CH3:2]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-].[C]>[NH2:45][C:42]1[CH:41]=[CH:40][C:39]([C:5]2[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]4[N:14]([S:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)(=[O:31])=[O:32])[C:15]([C:17]5[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=5)=[CH:16][C:9]=34)=[CH:7][N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:44][CH:43]=1

Participants

4

Reactant 1

HCID 689984001,1-dimethylethyl 4-[4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 689969611,1-dimethylethyl 4-[4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1 (2H)-pyridinecarboxylate (0.46 mmol) in ethyl acetate (5 mL) was purged with nitrogen and palladium(II) hydroxide/Carbon (30 mg of 20 wt. % palladium) added. The reaction was purged with hydrogen gas and allowed to stir vigorously under 1 atm of hydrogen. After 16 h, the reaction was purged with nitrogen and filtered though a pad of Celite (rinsing with ethyl acetate). The filtrate was concentrated under reduced pressure to give the title compound as a yellow foam which was used without further purification. ESMS [M+H]+: 625.6

Workup

  1. additionadded
  2. customThe reaction was purged with hydrogen gas
  3. customthe reaction was purged with nitrogen
  4. filtrationfiltered though a pad of Celite (rinsing with ethyl acetate)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09a70829f0104699a45dca36c1abf0ee
Source dataset
uspto-grants-2007_10
Patent number
US07282588B2

Reaction notes

Loading…