Sodium Carbonate → HCID 86669723, compound

HRID 1498052Notes

Reaction equation

HRID 1498052 reaction equation
[CH3:1][NH:2][C:3]1[C:8]2=[CH:9][N:10]=[C:11]([CH3:12])[N:7]2[N:6]=[CH:5][N:4]=1.[CH:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=O.[C:24](=[O:27])([O-])[O-].[Na+].[Na+]>C(O)C.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>[CH3:5][N:6]1[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH:24]=[O:27])=[CH:17][CH:16]=2)=[C:3]([C:9]2[N:10]=[C:11]([CH3:12])[N:7]3[C:8]=2[C:3]([NH:2][CH3:1])=[N:4][CH:5]=[N:6]3)[CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86669724HCID 86669724, compound

Product 1

HCID 86669723HCID 86669723, compoundYield 141.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

5-Bromo-1-methyl-1H-pyrazol-4-yl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine (1.18 g, 3.66 mmol), (4-formylphenyl)boronic acid (604 mg, 4.03 mmol), tetrakis(triphenylphosphine)palladium(0) (423 mg, 0.366 mmol) and sodium carbonate (776 mg, 7.32 mmol) were combined in ethanol (20 mL), and the reaction mixture was heated at reflux for 18 hours. After cooling, solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 0% to 100% [18:1:1 ethyl acetate/methanol/triethylamine] in heptane) provided the crude product (900 mg), which was taken directly to the next step. LCMS m/z 348.2 (M+1). 1H NMR (400 MHz, CD3OD), product peaks only: δ 2.57 (s, 3H), 2.82 (s, 3H), 3.95 (s, 3H), 7.51 (br d, J=8.2 Hz, 2H), 7.75 (s, 1H), 7.78 (s, 1H), 7.92 (br d, J=8.5 Hz, 2H), 9.98 (s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. customsolvent was removed in vacuo
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification via silica gel chromatography (Gradient: 0% to 100% [18:1:1 ethyl acetate/methanol/triethylamine] in heptane)

Sources & evidence

ORD record
ord-8783f4eb0e69406c95415a3cc23b3799
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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