2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol → HCID 71254249, compound

HRID 1775061Notes

Reaction equation

HRID 1775061 reaction equation
[CH3:1][C:2]([OH:19])([CH3:18])[CH2:3][N:4]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[N:5]1.Cl[C:21]1[C:29]2[C:24](=[CH:25][N:26]=[C:27]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:28]=2)[N:23](C2CCCCO2)[N:22]=1>>[CH3:18][C:2]([OH:19])([CH3:1])[CH2:3][N:4]1[CH:8]=[C:7]([C:21]2[C:29]3[C:24](=[CH:25][N:26]=[C:27]([C:30]4[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=4)[CH:28]=3)[NH:23][N:22]=2)[CH:6]=[N:5]1

Participants

3

Reactant 2

HCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-olHCID 71254297HCID 71254297, compound

Product 1

HCID 71254249HCID 71254249, compoundYield 40.7%

Procedure

Following the procedures in Example 172, 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol and 3-chloro-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine were reacted and deprotected to give 250 as a white solid (40.7% over two steps). 1H NMR (500 MHz, DMSO) δ 13.39 (s, 1H), 8.97 (s, 1H), 8.39 (s, 1H), 8.30 (s, 1H), 8.16 (d, J=10.2 Hz, 2H), 8.10 (s, 1H), 4.78 (s, 1H), 4.13 (s, 2H), 3.90 (s, 3H), 1.13 (s, 6H). LC/MS: m/z 338.1 [M+1]

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9e60697fd4444cefb2f8fa998697a4e7
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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