Water → 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

HRID 1630836Notes

Reaction equation

HRID 1630836 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:16])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[K+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:17])[CH:3]=1)[NH:16][C:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 962Water2×HCID 23665647Potassium tert-butoxideHCID 582155984-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine

Product 1

HCID 595346575-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine (3.1 g, 12.57 mmol) in NMP (40 mL) is added potassium tert-butoxide (2.1 g, 18.85 mmol) and the mixture is stirred overnight. Water (1 mL) is added to quench the reaction and the mixture is poured into water (100 mL). The mixture is extracted with diethyl ether five times. The combined organic phase is partially concentrated, resulting in precipitation of the product, which is filtered through a glass sintered funnel and washed with dichloromethane to afford 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.10-7.15 (m, 2H), 7.47-7.53 (m, 2H), 8.31 (dt, J=8.2, 1.9, 1.8 Hz, 1H), 8.55 (d, J=4.3 Hz, 1H), 9.16 (s, 1H), 12.23 (s, 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture is extracted with diethyl ether five times
  4. concentrationThe combined organic phase is partially concentrated
  5. customresulting in precipitation of the product, which
  6. filtrationis filtered through a glass sintered funnel
  7. washwashed with dichloromethane

Sources & evidence

ORD record
ord-2b7a4759798243a093aa8f887932ae2a
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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