2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde → HCID 17932557、化合物

HRID 1017575

反応式

HRID 1017575 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:30][CH:29]([CH:31]=O)[CH2:28][O:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[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][CH2:31][CH:29]3[CH2:28][O:27][C:26]([CH3:33])([CH3:25])[O:30]3)[CH:17]=2)=[CH:3]1

参加物

5

反応物 3

HCID 1107022,2-Dimethyl-1,3-dioxolane-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5327711Iron oxide, spent

生成物 1

HCID 17932557HCID 17932557、化合物収率 24%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and 2,2-dimethyldioxolane-4-carboxaldehyde (0.38 mmol) (prepared as described in Kumont, von R., et al. Helv. Chim. Acta., 66, 814, (1983)) in dichloromethane (12 mL) was stirred at room temperature for 10 min., and then Na(OAc)3BH (120 mg, 0.57 mmol) was added. The reaction mixture was stirred overnight and then partition between EtOAc and H20. The organic layer was separated, washed with water and concentrated. The crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyldioxolan-4-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione (32.6 mg, 24%).

後処理

  1. stirringThe reaction mixture was stirred overnight
  2. custompartition between EtOAc and H20
  3. customThe organic layer was separated
  4. washwashed with water
  5. concentrationconcentrated
  6. customThe crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-bb4da6f1b1944bd3b2902e2850851aa2
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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