2-Bromo-isonicotinic acid methyl ester → Methyl 2-(4-methylthiazol-2-yl)isonicotinate

HRID 594291ノート

反応式

HRID 594291 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:12][C:13]1[N:14]=[C:15]([Sn](CCCC)(CCCC)CCCC)[S:16][CH:17]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:13]1[N:14]=[C:15]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[S:16][CH:17]=1

参加物

5

反応物 2

HCID 38477682-Bromo-isonicotinic acid methyl esterHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazole

生成物 1

HCID 69081774Methyl 2-(4-methylthiazol-2-yl)isonicotinate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of commercially available methyl 2-bromoisonicotinate (2.750 g; 12.70 mmol), 4-methyl-2-(tributylstannyl)thiazole (4.942 g; 12.70 mmol), copper iodide CuI (242 mg; 1.27 mmol), and Pd(PPh3)4 (1.471 g; 1.27 mmol) in anh. DMF (55 ml) was heated to 90° C., under nitrogen, for 18 h. After cooling to rt, the reaction mixture was filtered over a pad of celite, and the separated solids were washed with AcOEt. The organic layer was washed with water and brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 2-(4-methylthiazol-2-yl)isonicotinate as a yellow solid. LC-MS (conditions A): tR=0.74 min.; [M+H]+: 234.94 g/mol.

後処理

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction mixture was filtered over a pad of celite
  3. washthe separated solids were washed with AcOEt
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (heptane/AcOEt=7/3)

出典と根拠

ORDレコード
ord-1a99e02aeba446ea9e2a5ea23c16c7cd
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

読み込み中…