Tetrahydrofuran → HCID 49805377, compound

HRID 1627825Notes

Reaction equation

HRID 1627825 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](OC(F)(F)F)=[CH:17][CH:16]=2)[C:3]=1[CH2:26][C:27]([O:29][CH3:30])=[O:28].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:41]1[CH2:45]OC[CH2:42]1.I[CH2:47][CH2:48][CH3:49]>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[C:20]3[C:2](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:7]([CH2:47][CH2:48][CH3:49])[C:6]=2[CH3:5])[C:3]=1[CH:26]([CH2:42][CH2:41][CH3:45])[C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597328HCID 66597328, compound

Product 1

HCID 49805377HCID 49805377, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl [2-methyl-4-(4-trifluoromethoxyphenyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (0.233 g; 0.57 mmol), LHMDS 1N in THF (0.85 mL; 0.85 mmol), 1-iodopropane (0.111 mL; 1.14 mmol) in DMF (2.8 mL) for 18 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (3-50%) in heptane furnished 0.129 g (50%) 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 (3-50%) in heptane

Sources & evidence

ORD record
ord-70e05a1f1c6f438dad7723a6723d2b4e
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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