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

HRID 1008994

反応式

HRID 1008994 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7e8277cacd9844d8b8c9787fe29a0c3e
出典データセット
uspto-grants-2011_07
特許番号
US07973026B2

関連ノート

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