Potassium Carbonate → (E)-3,4-bis(benzyloxy)-6-(4-(trifluoromethyl)styryl)pyridazine

HRID 927095Notes

Reaction equation

HRID 927095 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]([F:38])([F:37])[C:26]1[CH:36]=[CH:35][C:29](/[CH:30]=[CH:31]/B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:31]=[CH:30]/[C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:37])[F:38])=[CH:36][CH:35]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 6153620trans-2-[4-(Trifluoromethyl)phenyl]vinylboronic acidHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×

Product 1

HCID 86677029(E)-3,4-bis(benzyloxy)-6-(4-(trifluoromethyl)styryl)pyridazineYield 79.1%

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) (5 g, 15.30 mmol), (E)-4-(trifluoromethyl)styrylboronic acid (4.96 g, 22.95 mmol), potassium carbonate (7.40 g, 53.6 mmol) and tetrakis(triphenyl phosphine)palladium(0) (0.530 g, 0.459 mmol). The reaction was evacuated and purged with nitrogen before dioxane (3.40 ml) was added and the whole was heated under vacuum. Water (1.7 ml) was then added and the reaction mixture heated at 120° C. under microwave irradiation for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water and then brine and the combined organics were dried (MgSO4) and concentrated in vacuo to give the desired compound as an orange solid (5.6 g, 79%).

Workup

  1. customThe reaction was evacuated
  2. custompurged with nitrogen before dioxane (3.40 ml)
  3. additionwas added
  4. temperaturethe whole was heated under vacuum
  5. additionWater (1.7 ml) was then added
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washwashed with water
  8. dry with materialbrine and the combined organics were dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd8bca124e4442d7a560281d6f2f159a
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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