4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 44181708, compound

HRID 876923Notes

Reaction equation

HRID 876923 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[N:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1>>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:24]3[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=3)[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=23)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44181708HCID 44181708, compound

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with pyridine-4-boronic acid pinacol ester using General Procedure A. Purification on silica yielded 123. NMR: (CDCl3): 3.89 (s, 3H, CH3), 4.14 (s, 3H, CH3), 6.89-6.92 (m, H, ArH), 7.16 (m, H, ArH), 7.25 (s, H, ArH), 7.41 (t, H, ArH, J=8.1 HZ), 7.49 (sbr, H, NH), 8.39 (dd, 2H, 2×ArH, J=1.5 Hz, 4.5 Hz), 8.80 (dd, 2H, 2×ArH, J=1.5 Hz, 4.5 Hz). MS: (ESI+) MH+=333.24

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-3feb4c5f7d1d43208caaf80546234b4e
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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