Water → tert-butyl 4-(5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79595Notes

Reaction equation

HRID 79595 reaction equation
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[CH:6][N:5]=[C:4]2[N:15]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:16]=[CH:17][C:3]=12.[N:27]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.O>CN1C(=O)CCC1>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:2]([N:30]2[CH2:29][CH2:28][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32][CH2:31]2)=[C:3]2[CH:17]=[CH:16][N:15]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:19])=[O:20])[C:4]2=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 143452tert-Butyl piperazine-1-carboxylateHCID 68760247HCID 68760247, compound

Product 1

HCID 68761346tert-butyl 4-(5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylateYield 35.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

4-Fluoro-5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.200 g, 0.540 mmol) and tert-butyl piperazine-1-carboxylate (0.121 g, 0.648 mmol) were placed in NMP (2 mL). The reaction was then placed in the microwave and heated to 160° C. for 1 hour. The reaction was then cooled, poured into water and extracted with ether. The combined organic fractions were dried, filtered, and concentrated to give a crude oil that was purified by column chromatography (3:1 hexane:EtOAc) to give tert-butyl 4-(5-(2-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.102 g, 35.2% yield).

Workup

  1. temperatureThe reaction was then cooled
  2. extractionextracted with ether
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil that
  7. customwas purified by column chromatography (3:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-a6ee3ecceb074127ae3d54990d9de066
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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