3-Amino-6-chloro-4-picoline → 6-(2-Fluoro-5-methoxyphenyl)-4-methylpyridin-3-amine

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1B(O)O>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1

Participants

Reactant 2

HCID 27344253-Amino-6-chloro-4-picoline

HCID 41572112-Fluoro-5-methoxyphenylboronic acid

Product 1

HCID 584158716-(2-Fluoro-5-methoxyphenyl)-4-methylpyridin-3-amineYield 76%

Procedure

Obtained (1.225 g, yield 76%) following the procedure described in Intermediate 27, starting with 6-chloro-4-methylpyridin-3-amine (7.01 mmol, 1.000 g), 2-fluoro-5-methoxyphenylboronic acid (7.01 mmol, 1.191 g).

Workup

customObtained (1.225 g, yield 76%)

Sources & evidence

ORD record: ord-1326f287e68d439b9f2ecc60f9cc5155
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536165B2

Reaction notes

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