5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 44181706, compound

HRID 876921Notes

Reaction equation

HRID 876921 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.[NH:21]1[C:29]2[C:24](=[CH:25][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][N:28]=2)[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:26]3[CH:25]=[C:24]4[CH:23]=[CH:22][NH:21][C:29]4=[N:28][CH:27]=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 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44181706HCID 44181706, compound

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with 7-azaindole-5-boronic acid pinacol ester using General Procedure A. Purification on silica yielded 121. NMR: (CDCl3): 3.91 (s, 3H, CH3), 4.15 (s, 3H, CH3), 6.66 (m, H, ArH), 6.89 (m, H, ArH), 7.17 (m, H, ArH), 7.24 (s, H, ArH), 7.38-7.42 (m, 3H, 3×ArH), 7.51 (s, H, ArH), 9.04 (sbr, H, NH), 9.13 (m, H, ArH), 9.56 (m, H, ArH). MS: (ESI+) MH+=372.25

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-9da5285b2e1e4e7d97826f8a4f680fbc
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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