Tetrahydrofuran → HCID 49805374, compound

HRID 1627834Notes

Reaction equation

HRID 1627834 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][CH2:26][CH3:27])=[O:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:38]1[CH2:42]O[CH2:40][CH2:39]1.BrCC1CC1>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]([CH2:40][CH:39]1[CH2:42][CH2:38]1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81503BromomethylcyclopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597487HCID 66597487, compound

Product 1

HCID 49805374HCID 49805374, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from ethyl [2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (0.190 g; 0.5 mmol), LHMDS 1N in THF (0.55 mL; 0.55 mmol), bromomethylcyclopropane (0.096 mL; 1 mmol) in DMF (2 mL) for 18 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1-30%) in heptane furnished 0.036 g (16%) of the title compound as a colorless oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (1-30%) in heptane

Sources & evidence

ORD record
ord-7c2f99f18d664e219ff300f9ef62ab87
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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