Tetrahydrofuran → HCID 66597195, compound

HRID 1627831Notes

Reaction equation

HRID 1627831 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:3]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[F:42][C:43]([F:48])([F:47])[CH2:44][CH2:45]I>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[C:3]=1[CH:22]([CH2:45][CH2:44][C:43]([F:48])([F:47])[F:42])[C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597281HCID 66597281, compound

Product 1

HCID 66597195HCID 66597195, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl [2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (0.183 g; 0.5 mmol), LHMDS 1N in THF (0.75 mL; 0.75 mmol), 1,1,1-trifluoro-3-iodopropane (0.117 mL; 1 mmol) in DMF (2.5 mL) for 18 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (3-30%) in heptane furnished 0.061 g (25%) 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 (3-30%) in heptane

Sources & evidence

ORD record
ord-485252c4b72649a9b1d25af61a73e6be
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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