반응식
[CH2:1]([OH:4])[CH:2]=[CH2:3].C([Li])CCC.Br[CH2:11][C:12]1[C:16]2[N:17]([CH3:27])[CH:18]=[C:19]([C:22]([O:24]CC)=O)[C:20](=[O:21])[C:15]=2[S:14][CH:13]=1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>C1COCC1.CN(C=O)C.CCOCC>[CH2:1]([O:4][CH2:11][C:12]1[C:16]2[N:17]([CH3:27])[CH:18]=[C:19]([C:22]([NH:34][CH2:33][C:32]3[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=3)=[O:24])[C:20](=[O:21])[C:15]=2[S:14][CH:13]=1)[CH:2]=[CH2:3]참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 120 °C
실험 절차
To a cold (0° C.), stirred solution of 0.82 mL of allyl alcohol in 12 mL of dry THF, under argon, is added 2.1 mL of a 2.5 M solution of butyllithium in hexanes. The solution is stirred for 5 min, then added via cannula to a cold (0° C.), stirred mixture of 1.25 g of ethyl 3-(bromomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 19) in 8 mL of dry DMF. The resulting solution is stirred at 0° C. for 20 min, then quenched with dil. HCl. Aqueous workup (EtOAc/dil HCl) followed by flash chromatography on silica using 3% MeOH in CH2Cl2 affords a mixture of ethyl and allyl esters (873 mg). A mixture of 165 mg of the mixed esters and 580 mg of p-chlorobenzylamine is heated at 120° C. for 18 h, then cooled and diluted with ether. The resulting solid is filtered, washed well with ether, and dried in vacuo. Flash chromatography of the solid on silica using 2% MeOH in CH2Cl2 provides 922 mg of the title compound as a pale yellow solid. Recrystallization from EtOAc affords glistening yellow prisms.
후처리
- additionadded via cannula to a cold (0° C.)
- stirringstirred
- stirringThe resulting solution is stirred at 0° C. for 20 min
- customquenched with dil. HCl
- customaffords
- temperaturecooled
- filtrationThe resulting solid is filtered
- washwashed well with ether
- customdried in vacuo
출처 및 근거
- ORD 기록
- ord-bfdc5338683a418fa35090f67c40fe78
- 출처 데이터셋
- uspto-grants-2005_02
- 특허 번호
- US06852731B2
연결된 노트
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