2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde → HCID 17932557, 화합물

HRID 1017575

반응식

HRID 1017575 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 17932557HCID 17932557, 화합물수율 24%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bb4da6f1b1944bd3b2902e2850851aa2
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479490B2

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