Hydrochloric Acid → HCID 65197583, compound

HRID 1672002Notes

Reaction equation

HRID 1672002 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[N:7]1.B(F)(F)F.CCOCC.Cl.[OH-].[Na+]>CCOCC>[CH3:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2([NH2:12])[CH2:2][CH2:1]2)=[N:7]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 127475101-Methyl-1H-pyrazole-3-carbonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 65197583HCID 65197583, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl magnesium bromide (2.5 mol, 1 M in ether) was added at −78° C. to a solution of a 1-methyl-1H-pyrazole-3-carbonitrile (0.5 g, 1 mmol) and Ti(Oi-Pr)4 (1.1 mmol) in Et2O (5 mL). The yellow solution was stirred for 10 min. After the solution was warmed to ambient temperature (1 h), BF3.OEt2 (2 mmol) was added. After the mixture was stirred for 1 h, 1 N HCl and ether were added. NaOH (10%) was added to the resulting two clear phases and the mixture was extracted with ether. The combined ether layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Et2O). 1H NMR (400 MHz, CDCl3): δ 0.94-1.05 (m, 4H), 2.32 (s, 2H), 3.83 (s, 3H), 5.92 (d, 1H), 7.23-7.24 (d, 1H). LCMS: (ES+) m/z observed 137.7.

Workup

  1. additionwas added
  2. stirringAfter the mixture was stirred for 1 h
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe combined ether layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (Et2O)

Sources & evidence

ORD record
ord-5dad7417c49a47cc912a25452f93724b
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

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