Aniline → N-phenyl-1H-pyrrolo(2,3-b)pyridin-3-amine

HRID 250709Notes

Reaction equation

HRID 250709 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.S1(CCCC1)(=O)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([NH:18][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 31347SulfolaneHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 24180721N-phenyl-1H-pyrrolo(2,3-b)pyridin-3-amine

Conditions

Temperature
180 °C

Procedure

To 10 mg of 3-bromo-1H-pyrrolo[2,3-b]pyridine 582 was added 0.4 mL of sulfolane and aniline (2-3 equiv). The vial was sealed and heated at 180° C. for 10 minutes. After cooling, the desired compound was isolated by preparative HPLC/MS.

Workup

  1. customThe vial was sealed
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-46dbf28421f64ae1ba5b19885c4dccf0
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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