Sodium Hydroxide → (6-Chloro-pyrimidin-4-yl)-(2-propyl-2,3-dihydro-indol-1-yl)-methanone

HRID 1640254

Reaction equation

HRID 1640254 reaction equation
[CH2:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1)[CH2:2][CH3:3].[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20](Cl)=[O:21])[CH:15]=1.[OH-].[Na+]>ClCCl>[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][CH:4]2[CH2:1][CH2:2][CH3:3])=[O:21])[CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 127154212-PropylindolineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117516(6-Chloro-pyrimidin-4-yl)-(2-propyl-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.76 g (4.7 mmol) 2-propyl-2,3-dihydro-1H-indole in 15 mL dichloromethane was added to 0.88 g (5.0 mmol) 6-chloro-pyrimidine-4-carboxylic acid chloride in 15 mL dichloromethane at 0° C. and then 4.7 mL (4.7 mmol) of a 1M sodium hydroxide solution were added dropwise. The reaction mixture was stirred for 30 min at 0° C. and then for 1 h at RT. The organic phase was separated off and evaporated down. The residue was purified on silica gel.

Workup

  1. waitfor 1 h at RT
  2. customThe organic phase was separated off
  3. customevaporated down
  4. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-2a30de3be3614b55af634f233c6392f1
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Linked notes

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