Water → N-[6-(3-Hydroxypyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 2041933Notes

Reaction equation

HRID 2041933 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=3)=[O:10])=[CH:4][CH:3]=1.[OH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1.O>CN1CCCC1=O>[OH:29][CH:30]1[CH2:34][CH2:33][N:32]([C:2]2[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[N:12]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=4)=[O:10])=[CH:4][CH:3]=2)[CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 982104-HydroxypyrrolidineHCID 86631224N-[6-chloropyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

Product 1

HCID 57431515N-[6-(3-Hydroxypyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 0.4 g (1.01 mmol) of N-[6-chloropyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide, prepared in step 3.1, and 0.81 ml (10.06 mmol) of 3-hydroxypyrrolidine in 1.2 ml of N-methylpyrrolidinone is heated for 20 minutes in a microwave oven regulated at 200° C. under 300 watts. The reaction mixture is then poured into 50 ml of water. A solid is recovered by filtration and purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol. The resulting solid is then recrystallized from a mixture of methanol and dichloromethane. 0.22 g of a solid is recovered by filtration and dried under reduced pressure.

Workup

  1. temperatureis heated for 20 minutes in a microwave oven
  2. customregulated at 200° C. under 300 watts
  3. filtrationA solid is recovered by filtration
  4. custompurified by silica column chromatography, elution
  5. additionbeing carried out with a mixture of dichloromethane and methanol
  6. customThe resulting solid is then recrystallized from a mixture of methanol and dichloromethane
  7. filtration0.22 g of a solid is recovered by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6e0392b7e29f4bbbb1d1c2213779dad6
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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