Propargyl bromide → 4,9-Dihydro-3-methyl-4-(prop-2-ynyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1084715Notes

Reaction equation

HRID 1084715 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=12.Br[CH2:18][C:19]#[CH:20].C([Li])CCC>O1CCCC1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([CH2:20][C:19]#[CH:18])[C:6]=12

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 126587009,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 178418339Butyllithium

Product 1

HCID 200624924,9-Dihydro-3-methyl-4-(prop-2-ynyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example la) from 4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 3-bromo-prop-1-yne in the presence of butyllithium and tetrahydrofuran in a yield of 50% of theory. The crude crystalline product was used for subsequent reactions without being further purified by chromatography.

Workup

  1. customwithout being further purified by chromatography

Sources & evidence

ORD record
ord-57fe840065ca4fbe9ee5422a49d492c2
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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