Dimethylformamide → HCID 22256609, compound

HRID 1611495Notes

Reaction equation

HRID 1611495 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12.C([N-]C(C)C)(C)C.[Li+].CCCCCCC.[O:28]1CCC[CH2:29]1.C(C1C=CC=CC=1)C.CN(C)C=O>O1CCCC1.O.ClCCl>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[C:11]([CH:29]=[O:28])[S:12][C:3]=12

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 118164017-Chlorothieno[3,2-b]pyridine-6-carbonitrileHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 22256609HCID 22256609, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile (200 mg, 1.03 mmol) in 6 mL of tetrahydrofuran at −78° C. is added dropwise 2.0 M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene (0.645 mL, 1.29 mmol). After stirring for 40 minutes, N,N-dimethylformamide (99 mg, 1.35 mmol) is added dropwise over 5 minutes. The reaction mixture is stirred at −78° C. for 4 hours, then dichloromethane is added and the reaction mixture is allowed to warm to room temperature. Water is added and the organic phase is separated and the aqueous phase is extracted with dichloromethane. The organic phases are combined and washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by preparative thin layer chromatography developing with 30% ethyl acetate in hexane to provide 62 mg of 7-chloro-2-formylthieno[3,2-b]pyridine-6-carbonitrile as a white solid, mp 188-189° C.; 1H NMR (DMSO-d6) δ 8.72 (s, 1H), 9.26 (s, 1H), 10.28 (s, 1H); MS 221.9, 223.9 (M−H)−.

Workup

  1. stirringThe reaction mixture is stirred at −78° C. for 4 hours
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a77e921ce79447118b37aebe4223d7a8
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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