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

HRID 130601Notes

Reaction equation

HRID 130601 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f0ca08afb0594af0ac53aaeb398245be
Source dataset
uspto-grants-2008_06
Patent number
US07381818B2

Reaction notes

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