Tetrahydrofuran → HCID 66597497, compound

HRID 1627789Notes

Reaction equation

HRID 1627789 reaction equation
[CH3:1][C:2]1[S:23][C:5]2=[N:6][C:7]([CH3:22])=[C:8]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[C:4]2[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[S:23][C:5]2=[N:6][C:7]([CH3:22])=[C:8]([CH:17]([CH2:35][CH2:34][CH3:38])[C:18]([O:20][CH3:21])=[O:19])[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597178HCID 66597178, compound

Product 1

HCID 66597497HCID 66597497, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl 2-(2,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate (0.188 g; 0.578 mmol), LHMDS 1N in THF (0.650 mL; 0.650 mmol), 1-iodopropane (0.092 mL; 0.943 mmol) in DMF (8 mL) for 4 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-15%) in heptane furnished 0.139 g (65%) of the title compound as a yellow oil.

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-3de84b1501ee46d4a4d41563fbce9183
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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