Indoline → (6-Chloropyrimidin-4-yl)-(2,3-dihydroindol-1-yl)-methanone

HRID 1640232Notes

Reaction equation

HRID 1640232 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.[OH-].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 10328IndolineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117518(6-Chloropyrimidin-4-yl)-(2,3-dihydroindol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.50 g (2.83 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 20 mL dichloromethane were cooled with an ice/ethanol bath and combined with 0.30 mL (2.68 mmol) 2,3-dihydro-1H-indole. 2.7 mL (2.7 mmol) of a 1M sodium hydroxide solution were added dropwise. The reaction mixture was stirred for 2 h with cooling and for 1 h at RT. Then 50 mL of an aqueous saturated sodium hydrogen carbonate solution were added. After 10 min stirring the organic phases was separated off and washed with water and 1 M hydrochloric acid. The organic phases was dried on magnesium sulphate, filtered and evaporated down i.vac.

Workup

  1. stirringAfter 10 min stirring the organic phases
  2. customwas separated off
  3. washwashed with water and 1 M hydrochloric acid
  4. customThe organic phases was dried on magnesium sulphate
  5. filtrationfiltered
  6. customevaporated down i.vac

Sources & evidence

ORD record
ord-7d576f66458542559c2521d0d6394212
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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