4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86710638, compound

HRID 1027232Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]2[N:15]=[N:14][C:13]([N:16]([CH3:27])[CH:17]3[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]3)=[CH:12][CH:11]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][NH:41][CH:42]=2)O1>>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([C:38]2[CH:39]=[N:40][NH:41][CH:42]=2)[CH:3]=[C:4]([O:28][CH3:29])[C:5]=1[C:10]1[N:15]=[N:14][C:13]([N:16]([CH3:27])[CH:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HCID 86710639HCID 86710639, compound

Product 1

HCID 86710638HCID 86710638, compoundYield 70%

Procedure

6-(4-Bromo-2,6-dimethoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (63 mg, 0.136 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (52.8 mg, 0.272 mmol) were reacted according to GENERAL METHOD 1-5 for Suzuki coupling. The title compound was obtained as a yellow solid after column chromatography (43 mg, 70% yield). MS (M+1)=451.5.

Sources & evidence

ORD record: ord-83f882e2acbe4d549ec2cab22a8a6c54
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Reaction notes

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