1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde → (Rac)-(1-benzenesulfonyl-1h-pyrrolo[2,3-b]pyridin-3-yl)-[6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-methanol

HRID 69246노트

반응식

HRID 69246 반응식
Br[C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg]Br)C.[C:21]1([S:27]([N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[C:32]([CH:39]=[O:40])=[CH:31]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:21]1([S:27]([N:30]2[C:34]3=[N:35][CH:36]=[CH:37][CH:38]=[C:33]3[C:32]([CH:39]([C:2]3[N:6]4[N:7]=[C:8]([C:11]5[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=5)[CH:9]=[CH:10][C:5]4=[N:4][CH:3]=3)[OH:40])=[CH:31]2)(=[O:28])=[O:29])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

5

반응물 3

HCID 103566461-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 686324863-Bromo-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazineHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 68640363(Rac)-(1-benzenesulfonyl-1h-pyrrolo[2,3-b]pyridin-3-yl)-[6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Bromo-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 8.1, 150 mg, 0.539 mmol) was dissolved in THF (15 mL) under Nitrogen. Ethylmagnesium bromide solution (3 M, 0.360 mL) was added and the mixture was stirred at rt for 30 min. Then 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (Stage 199.2, 173 mg, 0.539 mmol) in THF (2 mL) was slowly added and the mixture was stirred at rt for 3.5 h. The mixture was quenched with 10% NH4Cl solution. It was extracted with EtOAc twice. The combined organic layers was washed with brine, dried over Na2SO4, filtered and evaporated. The title compound was obtained as a yellow solid (tR 1.4 min (conditions 1), MH+=486).

후처리

  1. stirringthe mixture was stirred at rt for 3.5 h
  2. customThe mixture was quenched with 10% NH4Cl solution
  3. extractionIt was extracted with EtOAc twice
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-28f63240596541afa69c260f781cc0bf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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