Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine-2-carbaldehyde

HRID 2193733Notes

Reaction equation

HRID 2193733 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.C1C[O:14][CH2:13]C1.CN(C=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:13]=[O:14])[S:10][C:3]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 112752517-Chlorothieno[3,2-b]pyridine

Product 1

HCID 509888497-Chlorothieno[3,2-b]pyridine-2-carbaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-chlorothieno[3,2-b]pyridine (2) (2 g, 11.83 mmol) in THF (40 mL) n-BuLi (2.5M in hexanes, 5.7 mL, 14.2 mmol) was added dropwise at −78° C. and the reaction mixture stirred 1 h. DMF (2.7 mL, 35.5 mmol) was added and stirring continued 1 h more. The reaction mixture was poured into water, extracted with EtOAc, the combined organics dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was triturated with ether and filtered affording title compound 232 (2 g, 10.12 mmol, 86% yield). MS (m/z): 197.9 (36%), (M+MeOH+1) 230.0 (100%).

Workup

  1. stirringstirring continued 1 h more
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organics dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b90197c59c3e4cb9aa887ef104ee678c
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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