Methanol → 2-(6-chloropyridazin-3-yl)-5-(1H-pyrazol-1-yl)phenol

HRID 1027150Notes

Reaction equation

HRID 1027150 reaction equation
B(Cl)(Cl)Cl.[Cl:5][C:6]1[N:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][C:13]=2[O:23]C)=[CH:10][CH:11]=1.CO>C(Cl)Cl>[Cl:5][C:6]1[N:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][C:13]=2[OH:23])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 867105443-Chloro-6-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]pyridazine2×

Product 1

HCID 1363771412-(6-chloropyridazin-3-yl)-5-(1H-pyrazol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BCl3 (1 M in DCM, 91 mL, 91 mmol) was added to a solution of 3-chloro-6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazine (Intermediate 2-1, 8.6 g, 30 mmol) in DCM (150 mL) at 0° C. and the reaction was stirred for 5 h at RT. MeOH (50 mL) was added to the reaction at 0° C., then the reaction was warmed to RT and the solvent was evaporated under reduced pressure. The crude material was treated with hot CH3CN then cooled to 5° C. The mixture was filtered and 2-(6-chloropyridazin-3-yl)-5-(1H-pyrazol-1-yl)phenol Intermediate 2-2 (7.6 g, 86%) was afforded as yellow solid. MS [M+H]: 273.2; 1H NMR (400 MHz, DMSO-d6) δ 11.95 (s, 1H), 8.59 (d, J=2.0 Hz, 1H), 8.49 (d, J=9.0 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 8.04 (d, J=9.0 Hz, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.51 (dd, J=8.5, 2.0 Hz, 1H), 6.59 (t, J=2.0 Hz, 1H).

Workup

  1. temperaturethe reaction was warmed to RT
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe crude material was treated with hot CH3CN
  4. temperaturethen cooled to 5° C
  5. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-ff65ca64913f4c228ad0b8e757039099
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

Loading…