Tetrahydrofuran → HCID 66597332, compound

HRID 1627791Notes

Reaction equation

HRID 1627791 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:23])=[C:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[S:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:34]1[CH2:38]OC[CH2:35]1.ICCC>CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:23])=[C:8]([CH:18]([CH2:35][CH2:34][CH3:38])[C:19]([O:21][CH3:22])=[O:20])[C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597413Methyl 2-(3,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 66597332HCID 66597332, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl 2-(3,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate (0.080 g; 0.246 mmol), LHMDS 1N in THF (0.280 mL; 0.280 mmol), 1-iodopropane (0.040 mL; 0.410 mmol) in DMF (3.5 mL) for 3.5 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-15%) in heptane furnished 0.087 g (96%) of the title compound as a white solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-15%) in heptane

Sources & evidence

ORD record
ord-9ae54b159bf9455aa312692219a7c22b
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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