HCID 59126908, compound → Methyl 4-(4-chloro-2,5-difluorophenyl)-2-methylnicotinate

HRID 1398438Notes

Reaction equation

HRID 1398438 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[N:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[C:19]([F:20])=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[C:16]([F:30])[CH:15]=1>>[Cl:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[N:5]=[CH:4][CH:3]=2)=[C:16]([F:30])[CH:15]=1

Participants

3

Reactant 2

HCID 59126908HCID 59126908, compoundHCID 84070460Methyl 4-chloro-2-methylpyridine-3-carboxylate

Product 1

HCID 86710418Methyl 4-(4-chloro-2,5-difluorophenyl)-2-methylnicotinateYield 24%

Procedure

Prepared as described in Example 16, Part D by carrying out a Suzuki coupling between methyl 4-chloro-2-methylnicotinate (prepared as described in Example 14, Part A) and 2-(4-chloro-2,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (prepared as described in Example 16, Part A-Part C) to afford methyl 4-(4-chloro-2,5-difluorophenyl)-2-methylnicotinate (3 g, 4.13 mmol, 24% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.60 (d, J=5.2 Hz, 1H), 7.36 (m, 1H), 7.20 (m, 2H), 3.74 (s, 3H), 2.49 (s, 3H).

Workup

  1. customPrepared
  2. customprepared

Sources & evidence

ORD record
ord-1704c6e857cd496aa36572a63d07f19a
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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