2,2-Dimethyl-1,3-dioxan-5-one → 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione

HRID 1017577

反応式

HRID 1017577 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[CH3:25][C:26]1([CH3:33])[O:31][CH2:30][C:29](=O)[CH2:28][O:27]1.[BH3-]C#N.[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:29]3[CH2:30][O:31][C:26]([CH3:33])([CH3:25])[O:27][CH2:28]3)[CH:17]=2)=[CH:3]1

参加物

5

反応物 3

HCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

生成物 1

HCID 120181673-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione収率 68.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (200 mg, 0.63 mmol) and 2,2-dimethyl-1,3-dioxane-5-one (98 mg, 0.76 mmol) in MeOH (10 mL) was stirred at room temperature for 15 min., and then NaCNBH3 (79 mg, 1.26 mmol) was added. After stirring the reaction mixture overnight the volatiles were removed under vacuo and the residue was purified by preparatory TLC (1% MeOH/CH2Cl2) to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione (185 mg, 68%). MS(EI): M+ 431, MP: 201-203° C.

後処理

  1. stirringAfter stirring the reaction mixture overnight the volatiles
  2. customwere removed under vacuo
  3. customthe residue was purified by preparatory TLC (1% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-9b2e8560d3e44f178d286171522b73fa
出典データセット
uspto-grants-2002_11
特許番号
US06479490B2

関連ノート

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