(4-Amino-3-bromothieno[3,2-c]pyridin-7-yl)methanol → 4-Amino-3-bromothieno[3,2-c]pyridine-7-carbaldehyde

HRID 17151Notes

Reaction equation

HRID 17151 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([Br:11])=[CH:9][S:10][C:6]=2[C:5]([CH2:12][OH:13])=[CH:4][N:3]=1>C1COCC1.O=[Mn]=O>[NH2:1][C:2]1[C:7]2[C:8]([Br:11])=[CH:9][S:10][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 18450834(4-Amino-3-bromothieno[3,2-c]pyridin-7-yl)methanol

Product 1

HCID 184508354-Amino-3-bromothieno[3,2-c]pyridine-7-carbaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 277E (1 g, 3.86 mmol) in THF (100 mL) was treated with MnO2 (2.66 g, 42.1 mmol), stirred overnight at room temperature, and filtered through diatomaceous earth (Celite®). The pad was washed with THF and dichloromethane and the combined filtrates were concentrated to provide 0.88 g (89% yield) of the desired product. MS (ESI(+)) m/e 256.8, 258.8 (M+H)+.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. washThe pad was washed with THF and dichloromethane
  3. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-fabe84145ad840b4b3c077c5acb259a2
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

Loading…