Ammonium Chloride → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

HRID 2279168Notes

Reaction equation

HRID 2279168 reaction equation
CON(C)[C:4]([C:6]1[C:7]2[C:29]([CH3:30])=[N:28][N:27]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])[CH:11]=1)=[O:5].C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]=[C:8]3[N:27]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[N:28]=[C:29]([CH3:30])[C:7]3=[C:6]([CH:4]=[O:5])[CH:11]=2)=[C:13]([F:26])[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 900139076-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, compound

Product 1

HCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehydeYield 113.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (1.0 g) was dissolved in THF (25 mL). At 0° C. methylmagnesium bromide solution (1 M, 3.9 mL) was added slowly, the mixture was warmed to r.t. while stirring overnight. Saturated ammonium chloride solution was added, the mixture was extracted with dichloromethane, the organic phases were dried over magnesium sulfate and concentrated in a membrane pump vacuum. The residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient) giving 1-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (1.0 g, quantitative yield with impurities).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in a membrane pump vacuum
  4. customThe residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-2b699af02f5e405192059cc52b65d73b
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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