Water → 3-(2-Bromoacetyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097545Notes

Reaction equation

HRID 2097545 reaction equation
C([O:5][C:6]([C:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:13]=[CH:12][C:11]=2[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=[CH2:7])CCC.O.[Br:35]N1C(=O)CCC1=O>O1CCCC1>[Br:35][CH2:5][C:6]([C:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:13]=[CH:12][C:11]=2[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 666030473-(1-Butoxyvinyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 866270563-(2-Bromoacetyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 8.80 g (17.8 mmol) of 3-(1-butoxyvinyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 57-(a) were added 21.1 ml of water and 341 ml of tetrahydrofuran, and 100 ml of tetrahydrofuran solution containing 4.70 g (26.4 mmol) of N-bromosuccinimide was added dropwise to the mixture under cooling in ice-bath. After the dropwise addition, the mixture was stirred at the same temperature 2 hours. After completion of the reaction, the reaction mixture 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 6.64 g of the title compound as a white solid. (Yield: 72%)

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling in ice-bath
  3. additionAfter the dropwise addition
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionthe fractions containing the desired compound
  7. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b848cb7e08846cbbe2062ebbdced516
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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