Phenylboronic Acid → 3-Methyl-6-phenylpyridazine

HRID 1054110Notes

Reaction equation

HRID 1054110 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH3:8][C:5]1[N:4]=[N:3][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 2272543-Chloro-6-methylpyridazine

Product 1

HCID 113787443-Methyl-6-phenylpyridazine

Procedure

Synthesized using 3-chloro-6-methylpyridazine (1.00 g, 7.78 mmol) and phenylboronic acid (1.42 g, 11.67 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (2:1) as eluent. White solid. Yield: 1.00 g, 76%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.76 (s, 3H), 7.39 (d, J=8.5 Hz, 1H), 7.46-7.55 (m, 3H), 7.76 (d, J=8.5 Hz, 1H), 8.03-8.09 (m, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=22.0, 123.9, 126.9, 127.2, 128.9, 129.7, 134.4, 136.4, 157.2, 158.5; (ESI): m/z=170.96 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-787aefee94cb4557907798c0eaa45211
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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