4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86710644, compound

HRID 1027237Notes

Reaction equation

HRID 1027237 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[C:11]([O:16][CH3:17])[C:10]=1[C:18]1[N:23]=[N:22][C:21]([N:24]([CH3:35])[CH:25]2[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:44]2[CH:45]=[N:46][NH:47][CH:48]=2)O1>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:44]2[CH:45]=[N:46][NH:47][CH:48]=2)[CH:12]=[C:11]([O:16][CH3:17])[C:10]=1[C:18]1[N:23]=[N:22][C:21]([N:24]([CH3:35])[CH:25]2[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86710645HCID 86710645, compound

Product 1

HCID 86710644HCID 86710644, compound

Procedure

6-(2-(Benzyloxy)-4-bromo-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (129 mg, 50% pure, 0.12 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (46.4 mg, 0.24 mmol) were reacted according to GENERAL METHOD 1-5 for Suzuki coupling. 6-(2-(Benzyloxy)-6-methoxy-4-(1H-pyrazol-4-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine was obtained as a yellow solid (14 mg, 22% yield) after HPLC purification. MS (M+1)=527.4.

Sources & evidence

ORD record
ord-d48da1d038434bc4ad1e78a15656cc31
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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