Tetrahydrofuran → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-pentenyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097448Notes

Reaction equation

HRID 2097448 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([O:10][C:11]2[CH:12]=[C:13]([C:21]3[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:24]4[CH:25]=[N:26][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28](=[O:29])[C:23]=4[C:22]=3[CH:47]=O)[CH:14]=[CH:15][C:16]=2[O:17][CH:18]([F:20])[F:19])[CH2:9][CH2:8]1.O1[CH2:53][CH2:52][CH2:51][CH2:50]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH:7]1([O:10][C:11]2[CH:12]=[C:13]([C:21]3[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:24]4[CH:25]=[N:26][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:37])[CH3:35])[C:28](=[O:29])[C:23]=4[C:22]=3[CH:47]=[CH:50][CH2:51][CH2:52][CH3:53])[CH:14]=[CH:15][C:16]=2[O:17][CH:18]([F:19])[F:20])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 86627032HCID 86627032, compound

Product 1

HCID 666026752-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-pentenyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 53%

Reagents, catalysts & solvents 1

HCID 159628Butyltriphenylphosphonium bromideCatalyst

Procedure

To 10 ml of tetrahydrofuran solution containing 1.20 g (3.00 mmol) of butyltriphenylphosphonium bromide was added 0.38 g (3.40 mmol) of potassium tert-butoxide under room temperature, and the mixture was stirred at the same temperature for 30 minutes. Then, to the mixture was added 0.62 g (1.00 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-formyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in the same method as in Example 15-(a), and the mixture was stirred for further 4 hours. After completion of the reaction, the reaction suspension was filtered, and the filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=1:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.35 g of the title compound as a slightly yellowish oil. (Yield: 53%).

Workup

  1. stirringthe mixture was stirred for further 4 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionthe fractions containing the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-263b441d7f2d43969418a642044450f3
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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