(6-Amino-5-bromopyridin-3-yl)methanol → 6-Amino-5-bromopyridine-3-carbaldehyde
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[Br:10]>C1(C)C=CC=CC=1.O=[Mn]=O>[NH2:1][C:2]1[C:3]([Br:10])=[CH:4][C:5]([CH:8]=[O:9])=[CH:6][N:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of compound A of Example 5 (1.9 g, 9.36 mmol) in toluene (20 mL) was added activated MnO2 (2.2 g, 25.6 mmol) and the mixture was heated to 80° C. with vigorous stirring. After 2 h, the mixture was cooled to RT and filtered. The filtrate was concentrated in vacuo to obtain 6-amino-5-bromonicotinaldehyde as a solid (1.8 g, 96%). LC/MS; (M+H)+=203, 201 (1:1 ratio). 1H NMR (CD3OD, 300 MHz) δ 9.59 (s, 1H), 8.34 (s, 1H), 8.03 (s, 1H).
Workup
- temperaturethe mixture was cooled to RT
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-eb5a01899bbd4fa49a4d43b9bae4c5a2
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148361B2
Reaction notes
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