Ammonia → 3-Bromothieno[3,2-c]pyridin-4-amine
Reaction equation
[Br:1][C:2]1[C:6]2[C:7](Cl)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[NH3:12]>O1CCOCC1>[Br:1][C:2]1[C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To the solution of 3-bromo-4-chloro-thieno[3,2-c]pyridine (3.2 g) in dioxane (30 ml) was added 28% ammonia solution (10 ml) in an autoclave and put into the oil bath. The reaction mixture was allowed to heat up to 150° C. and stir for 4 days at 150° C. The resultant mixture was concentrated in vacuo and the residue was purified by chromatography on a silica gel column to afford 3-bromo-thieno[3,2-c]pyridin-4-ylamine (1.7 g) 1H NMR (400 MHz, DMSO-d6) ppm 7.84 (d, J=5.6 Hz, 1H), 7.78 (s, 1H), 7.27 (d, J=5.6 Hz, 1H), 6.51 (s, 2H). MS: m/z 229, 231 (M+H)+.
Workup
- concentrationThe resultant mixture was concentrated in vacuo
- customthe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-39d43f87a0cd492490ff5b8913b60b85
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592352B2
Reaction notes
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