Chloromethyl Methyl Ether → methyl 5-bromo-6-cyclohexyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008994

반응식

HRID 1008994 반응식
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[H-].[Na+].[CH3:22][O:23][CH2:24]Cl>CN(C=O)C>[Br:1][C:2]1[N:6]([CH2:22][O:23][CH3:24])[C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

생성물 1

HCID 67298629methyl 5-bromo-6-cyclohexyl-4-(methoxymethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as in Example 7, Step 1) was dissolved in DMF and sodium hydride (1.4 eq.) was added. The mixture was stirred at RT until evolution of gas had ceased, then chloromethyl methyl ether (excess) was added and stirring was continued. After 5 h all volatiles were evaporated i. vac. and the residual material was filtered through silica gel (PE:Et2O, 12:1). The product was obtained as a colourless solid (66%). 1H-NMR (400 MHz, CDCl3, 300 K, δ): 7.73 (s, 1H), 5.41 (s, 2H), 3.90 (s, 3H), 3.32 (s, 3H), 2.73-2.67 (m, 1H), 1.90-1.76 (m, 5H), 1.65-1.58 (m, 2H), 1.47-1.29 (m, 3H).

후처리

  1. stirringstirring
  2. customAfter 5 h all volatiles were evaporated i
  3. filtrationand the residual material was filtered through silica gel (PE:Et2O, 12:1)

출처 및 근거

ORD 기록
ord-7e8277cacd9844d8b8c9787fe29a0c3e
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973026B2

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