Sodium Hydroxide → (5-Chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone

HRID 74511

Reaction equation

HRID 74511 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15]2.[OH-].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:8]([C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[CH:6][N:5]=1)=[O:9])[CH2:16][CH2:15]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 1175965-ChloroindolineHCID 516892Sodium BicarbonateHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117515(5-Chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.50 g (8.48 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 50 mL dichloromethane were cooled with a bath of ice/ethanol and combined with 1.20 g (7.81 mmol) 5-chloro-2,3-dihydro-1H-indole. 7.90 mL (7.90 mmol) of a 1M sodium hydroxide solution were added dropwise. The reaction mixture was stirred for 2 h while being cooled 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 phase was separated off and extracted with water (1×30 mL) and with 1 M hydrochloric acid (1×50 mL). The organic phase was dried on magnesium sulphate, filtered and evaporated down i. vac.

Workup

  1. stirringAfter 10 min stirring the organic phase
  2. customwas separated off
  3. extractionextracted with water (1×30 mL) and with 1 M hydrochloric acid (1×50 mL)
  4. customThe organic phase was dried on magnesium sulphate
  5. filtrationfiltered
  6. customevaporated down i

Sources & evidence

ORD record
ord-2389ea89d2da4366bcf08416cf049dff
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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