2-Methylpyridine-5-boronic acid → 5-Amino-6'-methyl-3-trifluoromethyl-[2,3']bipyridinyl-6-carboxylic acid methyl ester

HRID 444939Notes

Reaction equation

HRID 444939 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7](Br)[N:6]=1)=[O:4].[CH3:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][N:19]=1.NC1C(C(O)=O)=NC(C2C=CC(F)=CC=2)=C(C(F)(F)F)C=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:21]2[CH:20]=[N:19][C:18]([CH3:17])=[CH:23][CH:22]=2)[C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][C:10]=1[NH2:11])=[O:4]

Participants

4

Reactant 3

HCID 27630812-Methylpyridine-5-boronic acidHCID 584423103-Amino-6-(4-fluoro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acidHCID 58964428Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate2×

Product 1

HCID 673835145-Amino-6'-methyl-3-trifluoromethyl-[2,3']bipyridinyl-6-carboxylic acid methyl ester

Procedure

This compound was prepared from 3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) and 2-methylpyridine-5-boronic acid analogously to 3-amino-6-(4-fluoro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid (Intermediate G); LC-MS Rt 0.96 min [M+H]+ 312 (Method 2 minLC_v002); 1H NMR (400 MHz, DMSO-d6) δ 8.41 (1H, s), 7.79 (1H, s), 7.69 (1H, dd), 7.32 (1H, d), 7.10 (2H, s), 3.82 (3H, s), 2.52 (3H, s).

Sources & evidence

ORD record
ord-5ae871d6c0c74df390b7b117f55b1f61
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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