Tetrahydrofuran → HCID 86602405, compound

HRID 2373220Notes

Reaction equation

HRID 2373220 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[CH:7]1([CH2:10][O:11][CH2:12][C:13]2[N:18]=[C:17]3[N:19]([CH2:22][CH3:23])[N:20]=[CH:21][C:16]3=[C:15]([C:24]3[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=3)[C:14]=2[CH:31]=O)[CH2:9][CH2:8]1.C1C[O:36][CH2:35][CH2:34]1>O>[CH:7]1([CH2:10][O:11][CH2:12][C:13]2[N:18]=[C:17]3[N:19]([CH2:22][CH3:23])[N:20]=[CH:21][C:16]3=[C:15]([C:24]3[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=3)[C:14]=2/[CH:31]=[CH:34]/[C:35]([O:4][CH2:2][CH3:5])=[O:36])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 86602406HCID 86602406, compound

Product 1

HCID 86602405HCID 86602405, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of triethyl phosphonoacetate (219 mg) in THF (2 ml) was added potassium tert-butoxide (103 mg) at 0° C. and the mixture was stirred at room temperature for 30 minutes. A solution of 6-[(cyclopropylmethoxy)methyl]-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (190 mg) in THF (4 ml) was added at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:1) to give ethyl (2E)-3-[6-[(cyclopropylmethoxy)methyl]-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylate (183 mg) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:1)

Sources & evidence

ORD record
ord-f462ce945cd0466dbc3ad42f3e7a2468
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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