Water → HCID 66657620, compound

HRID 420997Notes

Reaction equation

HRID 420997 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:26]([O:28][C:29]([C:31]1[N:32]([C:52]2[CH:57]=[CH:56][C:55]([O:58][CH:59]([CH3:61])[CH3:60])=[CH:54][CH:53]=2)[C:33]2[C:38]([C:39]=1C=O)=[CH:37][C:36]([C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][N:43]=1)=[CH:35][CH:34]=2)=[O:30])[CH3:27].O.[CH3:63]N(C=O)C>>[CH2:26]([O:28][C:29]([C:31]1[N:32]([C:52]2[CH:53]=[CH:54][C:55]([O:58][CH:59]([CH3:60])[CH3:61])=[CH:56][CH:57]=2)[C:33]2[C:38]([C:39]=1[CH:63]=[CH:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:37][C:36]([C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:49])([F:50])[F:51])=[CH:44][N:43]=1)=[CH:35][CH:34]=2)=[O:30])[CH3:27]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester2×HCID 86628825HCID 86628825, compound

Product 1

HCID 66657620HCID 66657620, compound

Procedure

(Carbethoxymethylene)triphenylphosphorane (330 mg, 0.95 mmol) was added to a suspension of 3-formyl-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl ester (427 mg, 0.95 mmol; see step (b) above) in DMF (15 mL) and the mixture was stirred at rt for 3 h. Another portion of (carbethoxymethylene)triphenylphosphorane (165 mg, 0.47 mmol) was added and the stirring continued for 12 h. The mixture was poured into H2O and extracted with EtOAc. The combined extracts were washed with H2O, brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 386 mg (80%).

Workup

  1. waitthe stirring continued for 12 h
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-3786ccc9fbd24f8098423761f413f7c1
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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