Tert-butyl(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane → 3-Methoxy-4-(6-((2,2,6,6-tetramethylpiperidin-4-yl)methyl)pyridazin-3-yl)phenol

HRID 1027277Notes

Reaction equation

HRID 1027277 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[C:11]([O:24][CH3:25])[CH:10]=1)(C)C)(C)(C)C.Cl[C:27]1[N:28]=[N:29][C:30]([CH2:33][CH:34]2[CH2:39][C:38]([CH3:41])([CH3:40])[NH:37][C:36]([CH3:43])([CH3:42])[CH2:35]2)=[CH:31][CH:32]=1>>[CH3:25][O:24][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[C:27]1[N:28]=[N:29][C:30]([CH2:33][CH:34]2[CH2:35][C:36]([CH3:43])([CH3:42])[NH:37][C:38]([CH3:41])([CH3:40])[CH2:39]2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 86710628Tert-butyl(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilaneHCID 867106923-Chloro-6-((2,2,6,6-tetramethylpiperidin-4-yl)methyl)pyridazine

Product 1

HCID 1363771693-Methoxy-4-(6-((2,2,6,6-tetramethylpiperidin-4-yl)methyl)pyridazin-3-yl)phenolYield 61.9%

Procedure

Following standard GENERAL METHOD 1-4 for Suzuki coupling using tert-butyl(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane (408 mg, 1.12 mmol) and 3-chloro-6-((2,2,6,6-tetramethylpiperidin-4-yl)methyl)pyridazine (200 mg, 0.75 mmol) affords 3-methoxy-4-(6-((2,2,6,6-tetramethylpiperidin-4-yl)methyl)pyridazin-3-yl)phenol (165 mg) MS [M+H+]=356.1.

Sources & evidence

ORD record
ord-628eae8a267b4d65998c374ac5c5fde1
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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