Cyclopropanecarboxaldehyde → cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol

HRID 1943922Notes

Reaction equation

HRID 1943922 reaction equation
C([Mg]Cl)(C)C.I[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1.[CH:16]1([CH:19]=[O:20])[CH2:18][CH2:17]1>C1COCC1.CCOC(C)=O.[Cl-].[NH4+]>[CH:16]1([CH:19]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[OH:20])[CH2:18][CH2:17]1

Participants

7

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 178418918HCID 178418918, compound2×HCID 178506575HCID 178506575, compound

Product 1

HCID 178520052cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanolYield 45.9%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

i-PrMgCl (0.32 mL, 0.64 mmol) was added to 3-iodo-1H-pyrazolo[3,4-b]pyridine (3.1 mL, 0.61 mmol) in THF (3 mL) at 0° C. After 10 minutes, another portion of i-PrMgCl (0.32 mL, 0.64 mmol) was added. After 10 minutes, neat cyclopropanecarbaldehyde (0.074 mL, 0.98 mmol) was added dropwise and stirred at 0° C. for 1 hour. The mixture was diluted with EtOAc (5 mL) and aqueous ammonium chloride, and extracted with EtOAc (2×5 mL). The resulting residue was purified via flash chromatography eluting with EtOAc to afford cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (0.052 g, 0.28 mmol, 44.9% yield).

Workup

  1. waitAfter 10 minutes
  2. extractionextracted with EtOAc (2×5 mL)
  3. customThe resulting residue was purified via flash chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-305c142aa19f4ebf8afec2d8f46b813d
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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