2-Bromo-isonicotinic acid methyl ester → Methyl 2-(5-methylthiazol-2-yl)isonicotinate

HRID 594294노트

반응식

HRID 594294 반응식
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[S:17][C:16]([Sn](CCCC)(CCCC)CCCC)=[N:15][CH:14]=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[S:17][C:16]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:15][CH:14]=1

참가 물질

5

반응물 2

HCID 38477682-Bromo-isonicotinic acid methyl esterHCID 164271315-Methyl-2-(tributylstannyl)-1,3-thiazole

생성물 1

HCID 69082465Methyl 2-(5-methylthiazol-2-yl)isonicotinate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of commercially available methyl 2-bromoisonicotinate (2.750 g; 12.70 mmol), 5-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-(5-methylthiazol-2-yl)isonicotinate as an orange solid. LC-MS (conditions A): tR=0.74 min.; [M+H]+: 235.10 g/mol.

후처리

  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)

출처 및 근거

ORD 기록
ord-b93bb39c4a4c4812bd60010272edf9fa
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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