Sodium Carbonate → methyl 6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008976

反応式

HRID 1008976 の反応式
Br[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.[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O)=[CH2:21].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:14]1([C:3]2[C:4]3[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:5]=3[NH:6][C:2]=2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:20]=[CH2:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27735872-Vinylbenzeneboronic acidHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

生成物 1

HCID 67298999methyl 6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate収率 71%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

Methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as described in Example 7, Step 1) and (2-vinylphenyl)boronic acid (1.5 eq.) were dissolved in dioxane (0.06 M) and 2M aq. Na2CO3 (6 eq.) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq.) was added, and the reaction mixture was placed in an oil bath preheated to 110° C. and stirred for 1 h; after removing all volatiles the title compound was isolated by chromatography (PE/EtOAc 10:1). Yield: 71%. 1H-NMR (400 MHz, CDCl3, 300 K, δ) 8.16 (bs, 1H), 7.69 (d, 1H, J 7.9), 7.68 (s, 1H), 7.45-7.35 (m, 3H), 6.67 (dd, 1H, J 17.5, 11.0), 5.74 (d, 1H, J 17.5), 5.25 (d, 1H, J 11.0), 3.91 (s, 3H), 2.54-2.47 (m, 1H), 1.81-1.23 (m, 10H); MS (ES+) m/z 366 (M+H)+.

後処理

  1. customThe solution was degassed
  2. additionwas added
  3. customthe reaction mixture was placed in an oil bath
  4. custompreheated to 110° C.
  5. customafter removing all volatiles the title compound
  6. customwas isolated by chromatography (PE/EtOAc 10:1)

出典と根拠

ORDレコード
ord-d95d8e1b59684113b8a0006376ae03ef
出典データセット
uspto-grants-2011_07
特許番号
US07973026B2

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