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

HRID 593565Notes

Reaction equation

HRID 593565 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-21a92947393f44f2ba31a5b9d1d27587
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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