Triethylamine → Methyl 3-(6-{[1-(4-methoxyphenyl)-2-methylene-1-phenylbut-3-enyl]amino}hexanoyl)pyrrolo[4,5-e]indoline-7-carboxylate

HRID 992907Notes

Reaction equation

HRID 992907 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](OC2C(F)=C(F)C=C(F)C=2F)=[O:29])([C:16]2[CH:21]=CC=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH:41]1[C:45]2=[C:46]3[C:50](=[CH:51][CH:52]=[C:44]2[NH:43][CH:42]=1)[NH:49][CH:48]([C:53]([O:55][CH3:56])=[O:54])[CH2:47]3.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([N:43]2[C:44]3[C:45](=[C:46]4[C:50](=[CH:51][CH:52]=3)[NH:49][CH:48]([C:53]([O:55][CH3:56])=[O:54])[CH2:47]4)[CH:41]=[CH:42]2)=[O:29])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[CH2:21])[CH:17]=[CH2:18])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 184081682,3,5,6-Tetrafluorophenyl 6-{[(4-methoxyphenyl)diphenylmethyl]amino}hexanoateHCID 66717311Methyl pyrrolo[4,5-e]indoline-7-carboxylate

Product 1

HCID 86588457Methyl 3-(6-{[1-(4-methoxyphenyl)-2-methylene-1-phenylbut-3-enyl]amino}hexanoyl)pyrrolo[4,5-e]indoline-7-carboxylateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7 (0.6 g, 1.1 mmol) was combined with 0.24 g (1.2 mmol) methyl pyrrolo[4,5-e]indoline-7-carboxylate (Boger et al, supra) and 0.1 ml triethylamine in 5 ml of anhydrous CH2Cl2. The mixture was kept at room temperature for 15 h and concentrated under vacuum. The resultant solid, which was the desired product, was washed with 50% ethyl acetate/50%hexane to remove unreacted starting materials and 2,3,5,6-tetrafluorophenol. Drying under vacuum afforded 0.51 g (77%) of the title compound as a pale-yellow, crystalline solid.

Workup

  1. concentrationconcentrated under vacuum
  2. washwas washed with 50% ethyl acetate/50%hexane
  3. customto remove unreacted
  4. customDrying under vacuum

Sources & evidence

ORD record
ord-3714c72eedbd4e59a604fb04bfdfd282
Source dataset
uspto-grants-2002_10
Patent number
US06472153B1

Reaction notes

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