Dimethylformamide → Methyl 3-{6-[bis(4-methoxyphenyl)phenylmethoxy]hexanoyl}pyrrolo[4,5-e]indoline-7-carboxylate

HRID 130601노트

반응식

HRID 130601 반응식
C1[C:5]2=[C:6]3[C:10](=[CH:11]C=C2NC=1)[NH:9][CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7]3.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:26][CH:27](CC)[CH2:28][CH2:29][C:30](OC2C=CC([N+]([O-])=O)=CC=2)=O)=[CH:21][CH:20]=1.[CH2:58]([N:60]([CH2:63][CH3:64])[CH2:61][CH3:62])[CH3:59].CN(C=[O:69])C>>[CH3:57][O:56][C:53]1[CH:52]=[CH:51][C:50]([C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:59][C:58]([N:60]2[C:63]3[C:5](=[C:6]4[C:10](=[CH:11][CH:64]=3)[NH:9][CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7]4)[CH:62]=[CH:61]2)=[O:69])=[CH:55][CH:54]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66717311Methyl pyrrolo[4,5-e]indoline-7-carboxylateHCID 686370484-Nitrophenyl 4-[bis(4-methoxyphenyl)phenylmethoxy]hexanoate

생성물 1

HCID 69198674Methyl 3-{6-[bis(4-methoxyphenyl)phenylmethoxy]hexanoyl}pyrrolo[4,5-e]indoline-7-carboxylate

실험 절차

A solution of methyl pyrrolo[4,5-e]indoline-7-carboxylate (2.7 g, 12.5 mmol) prepared according to Boger et al (J. Org. Chem. 52:1521 (1987)), 4-nitrophenyl 4-[bis(4-methoxyphenyl)phenylmethoxy]hexanoate (6.9 g, 12.5 mmol) and triethylamine (2 mL) in 50 mL of anhydrous DMF was stirred at room temperature for 5 h and then concentrated. The resulting oil was left at room temperature overnight (˜15 h). The oil was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed twice with diluted sodium bicarbonate, saturated sodium chloride and dried over sodium sulfate. The crude product obtained after removal of the solvent was crystallized from ethyl acetate. The yield of the crystalline product 15 was 5.9 g (75%). 1H NMR (DMSO-d6) δ 11.94 (s, 1H), 8.24 (d, J=9 Hz, 1H), 7.4-7.2 (m, 10H), 7.07 (s, 1H), 6.87 (d, J=9 Hz, 4H), 4.16 (t, J=8 Hz, 2H), 3.87 (s, 3H), 3.72 (s, 6H), 3.28 (t, J=8 Hz, 2H), 2.96 (t, J=6 Hz, 2H), 2.42 (t, J=7 Hz, 2H), 1.58 (m, 4H), 1.41 (m, 2H).

후처리

  1. concentrationconcentrated
  2. waitThe resulting oil was left at room temperature overnight (˜15 h)
  3. customThe oil was partitioned between ethyl acetate and 5% sodium bicarbonate
  4. washThe organic phase was washed twice with diluted sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-f0ca08afb0594af0ac53aaeb398245be
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381818B2

반응 노트

불러오는 중…