5-(Thiophen-2-yl)pent-4-ynyl methanesulfonate → Ethyl 9-isopropoxy-8-methoxy-2-(3-(methylsulfonyloxy)propyl)-1-(thiophen-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

HRID 1971654Notes

Reaction equation

HRID 1971654 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:19][CH:20]([CH3:22])[CH3:21])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]1C(O)=O)=O)[CH3:2].[CH3:27][S:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]#[C:36][C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)(=[O:30])=[O:29]>C(OC(=O)C)(=O)C>[CH:20]([O:19][C:11]1[CH:10]=[C:9]2[C:14]([CH2:15][CH2:16][N:7]3[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:26])=[C:35]([CH2:34][CH2:33][CH2:32][O:31][S:28]([CH3:27])(=[O:29])=[O:30])[C:36]([C:37]4[S:38][CH:39]=[CH:40][CH:41]=4)=[C:8]32)=[CH:13][C:12]=1[O:17][CH3:18])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 581248695-(Thiophen-2-yl)pent-4-ynyl methanesulfonateHCID 58124872HCID 58124872, compound

Product 1

HCID 58124861Ethyl 9-isopropoxy-8-methoxy-2-(3-(methylsulfonyloxy)propyl)-1-(thiophen-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylateYield 58.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 280 mg of 6b and 165 mg of 2b in 6 ml of acetic anhydride was heated in a microwave oven for 15 min at 140° C. The reaction mixture was cooled and residual solvents were removed by sequential coevaporation with toluene. The residue was purified by chromatography on silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 215 mg of 6c; MS-ESI: [M+1] 548.15.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customresidual solvents were removed by sequential coevaporation with toluene
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d60f97928aaf4531b5e8c711cc0495b6
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…