2-Fluoro-5-methylbenzeneboronic acid → HCID 71253767, compound

HRID 1775021Notes

Reaction equation

HRID 1775021 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1B(O)O.Cl[C:13]1[C:21]2[C:16](=[CH:17][N:18]=[C:19]([C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[CH:20]=2)[N:15](C2CCCCO2)[N:14]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:13]1[C:21]2[C:16](=[CH:17][N:18]=[C:19]([C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[CH:20]=2)[NH:15][N:14]=1

Participants

3

Reactant 2

HCID 103518842-Fluoro-5-methylbenzeneboronic acidHCID 71254297HCID 71254297, compound

Product 1

HCID 71253767HCID 71253767, compoundYield 21.3%

Procedure

Following the procedures in Example 172, 2-fluoro-5-methylphenylboronic acid 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 205 as a white solid (21.3% over two steps). 1H NMR (400 MHz, DMSO) 6 (400 MHz, DMSO) δ 13.86 (s, 1H), 9.05 (s, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.88 (d, J=2.7 Hz, 1H), 7.63 (d, J=6.3 Hz, 1H), 7.36-7.27 (m, 2H), 3.88 (s, 3H), 2.40 (s, 3H). LC/MS: m/z 308.0 [M+1]

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0a34dea041234a6ca60ba4aa3f3cb89a
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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