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 69246Notes

Reaction equation

HRID 69246 reaction equation
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

Participants

5

Reactant 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, compound

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-28f63240596541afa69c260f781cc0bf
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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