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

HRID 74604Notes

Reaction equation

HRID 74604 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH2:17][CH2:16]2.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([N:18]2[C:19]3[C:15](=[CH:14][C:13]([F:12])=[CH:21][CH:20]=3)[CH2:16][CH2:17]2)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27744635-FluoroindolineHCID 27816432,6-Dichloro-isonicotinoyl chloride

Product 1

HCID 58386613(2,6-Dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (9.5 mmol) 2,6-dichloro-pyridine-4-carboxylic acid chloride in 50 mL DCM were cooled in the ice/EtOH bath and combined with 1.3 g (9.6 mmol) 5-fluoro-2,3-dihydro-1H-indole. In addition 9.6 mL (9.6 mmol) of a 1N aqueous sodium hydroxide solution were added dropwise and the mixture was stirred for 2 h while being cooled and for 1 h at RT. 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 on sodium sulphate and evaporated down.

Workup

  1. additionwere added dropwise
  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 on sodium sulphate
  6. customevaporated down

Sources & evidence

ORD record
ord-aac0edd0abf941448d699b3cd2271efd
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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