Nitrogen → 3-(4-pyridinyl)-1H-indazole-5-carboxaldehyde

HRID 218454Notes

Reaction equation

HRID 218454 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[NH:4][N:3]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=3)[NH:4][N:3]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178519380HCID 178519380, compound

Product 1

HCID 249587413-(4-pyridinyl)-1H-indazole-5-carboxaldehydeYield 64.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Procedure

To a suspension of 3-iodo-1H-indazole-5-carboxaldehyde (200 mg, 0.74 mmol) and 4-pyridineboronic acid (110 mg, 0.89 mmol) in toluene/EtOH (1:1, 8 mL) in a sealed tube was added Na2CO3 (2 N, 1 mL) followed by Pd(PPh3)4 (85 mg, 0.074 mmol). The reaction mixture was put under vacuum, and re-charged with N2 three times, then kept at ca. 100-110° C. for ca. 4-5 hr. The reaction mixture was cooled to rt, diluted with water, and extracted with EtOAc. The organic phase was washed with brine, and dried. Concentration followed by purification by flash chromatography afforded 3-(4-pyridinyl)-1H-indazole-5-carboxaldehyde (106 mg, 64%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationConcentration
  5. customfollowed by purification by flash chromatography

Sources & evidence

ORD record
ord-219364dd8b984b338fcabb445a1c3809
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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