Hydrochloric Acid → HCID 65197583, compound

HRID 1025203Notes

Reaction equation

HRID 1025203 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-764ce3e3d6c843dfacbe2b1fed622ad6
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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