Water → N-(4-(4-formylphenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 873330Notes

Reaction equation

HRID 873330 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1>[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]([CH:14]4[CH2:16][CH2:15]4)=[O:13])[CH:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:21][CH:20]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 70979567N-(4-bromopyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 86710532N-(4-(4-formylphenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(4-Bromopyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (4.66 g, 17 mmol), 4-formylphenyl boronic acid (3.06 g, 20.4 mmol), PdCl2dppf (0.37 g, 0.45 mmol) and Na2CO3 (3.6 g, 34 mmol) were stirred in 1,4-dioxane (140 mL) and water (28 mL) at 100° C. for 3 h. The reaction mixture was cooled to room temperature, filtered through celite, washed through with DCM and concentrated in vacuo. The residue was triturated with EtOAc and dried in vacuo to afford N-(4-(4-formylphenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide.

Workup

  1. filtrationfiltered through celite
  2. washwashed through with DCM
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with EtOAc
  5. customdried in vacuo

Sources & evidence

ORD record
ord-07dcd14da5024273b67591daff630ad6
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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