3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine-6-carbaldehyde → 1-(3-((6-Fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-ol

HRID 456177Notes

Reaction equation

HRID 456177 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([CH:22]=[O:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.[CH2:24]([Mg]Br)[CH3:25]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([CH:22]([OH:23])[CH2:24][CH3:25])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 866660873-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine-6-carbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 669271811-(3-((6-Fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)propan-1-olYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine-6-carbaldehyde (52 mg, 0.168 mmol) in THF (4 mL) at 0° C., was added a solution of ethylmagnesium bromide in THF (1M, 0.336 mL) dropwise. After stirring for 16 h, the reaction mixture was quenched with NH4Cl(aq), extracted with EtOAc, dried over Na2SO4. Filtered through Celite and concentrated in vacuo to give a crude product (14 mg, 10%). LCMS (method B): [MH]+=340, tR=2.04 min.

Workup

  1. customthe reaction mixture was quenched with NH4Cl(aq)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationFiltered through Celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23857bb72e2043e287c11b9e0d824819
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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