Dimethylformamide → 2,3-Dihydro-1h-benzo[e]indole

HRID 366805

반응식

HRID 366805 반응식
C(OC([N:8]1[C:16]2[CH:15]=[C:14]([N+]([O-])=O)[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10](CCl)[CH2:9]1)=O)(C)(C)C.CCN=C=NCCCN(C)C.Cl.COC1C=C2C(=C(OC)C=1OC)NC(C(O)=O)=C2.CN(C=O)C>Cl.O>[CH2:10]1[C:11]2[C:12]3[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=3[CH:14]=[CH:15][C:16]=2[NH:8][CH2:9]1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8210525,6,7-Trimethoxy-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

생성물 1

HCID 111479652,3-Dihydro-1h-benzo[e]indole수율 196.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

반응 조건

온도
20 °C

실험 절차

A solution of 13 (170 mg, 0.47 mmol) in HCl-saturated dioxane (10 mL) was stirred at 20° C. for 2 h, then evaporated under reduced pressure below 30° C. EDCI-HCl (270 mg, 1.41 mmol), 5,6,7-trimethoxyindole-2-carboxylic acid (118 mg, 0.47 mmol) and DMF (2.5 mL) were then added, and the mixture was stirred at 20° C. for 2 h. Addition of water precipitated a crude product, which was recrystallised twice from CH2Cl2 /iPr2O to give 1-chloromethyl-5-nitro-3-[5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (14a) (156 mg, 67%), mp 243-245° C. 1H NMR (CDCl3) δ9.44 (s, 1 H, NH), 9.24 (s, 1 H, H-9), 8.43 (dd, J=7.9, 1.2 Hz, 1 H, H-7), 7.87 (dd, J=7.7, 1.5 Hz, 1 H, H-4), 7.70-7.60 (m, 2 H, H-5,6), 7.03 (d, J=2.5 Hz, 1 H, H-3'), 6.87 (s, 1 H, H-4'), 4.88 (dd, J=10.8, 2.1 Hz, 1 H, H-2), 4.74 (dd, J=10.4, 8.9 Hz, 1 H, H-2), 4.36-4.26 (m, 1 H, H-3), 4.10 (s, 3 H, OCH3), 3.99 (dd, J=11.4, 3.1 Hz, 1 H, CHHCl), 3.95 (s, 3 H, OCH3), 3.92 (s, 3 H, OCH3), 3.58 (dd, J=11.4, 9.9 Hz, 1 H, CHHCl).

후처리

  1. customevaporated under reduced pressure below 30° C
  2. customprecipitated a crude product, which
  3. customwas recrystallised twice from CH2Cl2 /iPr2O

출처 및 근거

ORD 기록
ord-f796f21a8dc64695804fb7508f9f685c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130237

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