Dichloromethane → 2-{5-Methyl-2-[4-(6-methyl-pyridazin-3-yl)-phenyl]-oxazol-4-yl}-ethanol

HRID 1445770Notes

Reaction equation

HRID 1445770 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:22][CH2:23][OH:24].I[C:26]1[N:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:26]3[N:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:22][CH2:23][OH:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 126802583-Iodo-6-methylpyridazineHCID 589514312-{5-Methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol2×

Product 1

HCID 589514672-{5-Methyl-2-[4-(6-methyl-pyridazin-3-yl)-phenyl]-oxazol-4-yl}-ethanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of 2-{5-Methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol (0.314 g, 0.952 mmol) (See Intermediate 3), 3-Iodo-6-methyl-pyridazine (0.178 g, 0.810 mmol) [CAS# 1618-47-9] and [1,1 bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (1:1) (0.02 g, 0.024 mmol) in 10 mL dioxane is added aqueous sodium carbonate (2M, 1.22 mL) and the reaction is carried out substantially in accordance with the procedure of Example 9 to provide after purification by radial chromatography pure titled compound (0.208 g, 87%). MS (m/e): 296.3 (M+1).

Workup

  1. customto provide
  2. customafter purification by radial chromatography pure titled compound (0.208 g, 87%)

Sources & evidence

ORD record
ord-f4c3878b20d74f3da91de20c9dd3656c
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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