Sodium Hydroxide → (6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 1640255Notes

Reaction equation

HRID 1640255 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[F: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+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27744635-FluoroindolineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117506(6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.92 g (4.9 mmol) 6-chloro-pyrimidine-4-carboxylic acid chloride in 40 mL DCM were cooled in an ice/acetone bath and mixed with 0.67 g (4.9 mmol) 5-fluoro-2,3-dihydro-1H-indole. Another 5 mL (5.0 mmol) of a 1N aqueous sodium hydroxide solution were added dropwise and the mixture was stirred for 1 h with cooling. Then 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for a further 10 min. The organic phase was separated off, extracted with 1N aqueous hydrochloric acid solution and with water, dried and evaporated down.

Workup

  1. temperaturewith cooling
  2. stirringthe mixture was stirred for a further 10 min
  3. customThe organic phase was separated off
  4. extractionextracted with 1N aqueous hydrochloric acid solution and with water
  5. customdried
  6. customevaporated down

Sources & evidence

ORD record
ord-c4016c93957347ceac27671320317ee3
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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