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

HRID 2390646Notes

Reaction equation

HRID 2390646 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-95817262f5d6454d9c1bff2d3a539ff1
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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