Potassium Carbonate → Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)isonicotinate

HRID 1963223ノート

反応式

HRID 1963223 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:23][C:24]=1[C:25]([F:28])([F:27])[F:26]>CO.Cl[Pd]Cl>[F:18][C:19]1[CH:20]=[C:21]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:22]=[CH:23][C:24]=1[C:25]([F:26])([F:27])[F:28]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 467390543-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol ester

生成物 1

HCID 66732503Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)isonicotinate収率 76.1%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

Methyl 2-chloroisonicotinate (2.86 g, 16.67 mmol), PdCl2 (dppf) (0.278 g, 0.38 mmol) and potassium carbonate (1.161 mL, 19.24 mmol) were distributed equally over 3 microwave reaction vials. 2-(3-Fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (3.72 g, 12.82 mmol) dissolved in methanol (45 mL) was split into 3 equal portions and added to the vials. The vials were capped and heated in a single node microwave reactor at 100° C. for 10 min each. The contents of the vials was combined and the solvent evaporated. The residue was dissolved in DCM and washed with water. The organic phase was filtered through a phase separator and evaporated. The residue was purified by automated flash chromatography on a Biotage® KP-SIL 340 g column. 7:1 of heptane:EtOAc over 10 CV was used as mobile phase. Crude methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)isonicotinate (2.92 g, 76%) was isolated. MS m/z 300 (M+H)+

後処理

  1. customwas split into 3 equal portions
  2. additionadded to the vials
  3. customThe vials were capped
  4. customthe solvent evaporated
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with water
  7. filtrationThe organic phase was filtered through a phase separator
  8. customevaporated
  9. customThe residue was purified by automated flash chromatography on a Biotage® KP-SIL 340 g column

出典と根拠

ORDレコード
ord-284d82b5404541aa96bfc01eee69f6a0
出典データセット
uspto-grants-2013_04
特許番号
US08415378B2

反応ノート

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