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

HRID 1640250Notes

Reaction equation

[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([F:12])=[CH:8][CH:9]=2)[NH:4]1)[CH3:2].[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:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([F:12])[CH:6]=3)[CH2:11][CH:3]2[CH2:1][CH3:2])=[O:21])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2.5 g (10 mmol) 2-ethyl-6-fluoro-2,3-dihydro-1H-indol in 25 mL dichloromethane was added at 0° C. to 1.8 g (10 mmol) 6-chloro-pyrimidine-4-carboxylic acid chloride in 25 mL dichloromethane and then 10 mL (10 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

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

Sources & evidence

ORD record: ord-ccdd1e340246450891542841117db6ee
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110575B2

Reaction notes

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