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

HRID 130601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130601
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

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f0ca08afb0594af0ac53aaeb398245be
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381818B2

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