Sodium Carbonate → HCID 86627906、化合物

HRID 1669475ノート

反応式

HRID 1669475 の反応式
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH:21]([C:23]1[C:24]([O:32][CH3:33])=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].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:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH:21]=[O:22])[C:24]=2[O:32][CH3:33])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateHCID 16218167(3-Formyl-2-methoxyphenyl)boronic acid

生成物 1

HCID 86627906HCID 86627906、化合物収率 77%

試薬・触媒・溶媒 2

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

反応条件

温度
110 °C

実験手順

Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPh3)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. 2M Na2CO3 solution (1 eq) was added and the mixture was heated to 110° C. for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1). After evaporation of the fractions containing product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate was obtained as off-white solid (77%). (ES+) m/z 392 (M+H)+.

後処理

  1. customThe solution was degassed
  2. customflushed with Ar
  3. customAll volatiles were evaporated in vacuo
  4. dissolutionthe residual material was dissolved in EtOAc
  5. filtrationfiltered over Celite
  6. customevaporated in vacuo
  7. filtrationThe residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1)
  8. customAfter evaporation of the fractions
  9. additioncontaining product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate

出典と根拠

ORDレコード
ord-bfee15f67e3a4700bec296c174cf6635
出典データセット
uspto-grants-2011_08
特許番号
US07989438B2

反応ノート

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