Ethanol → 4-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine

HRID 1443083노트

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HRID 1443083 반응식
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5](I)=[CH:4][N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.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>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 768504784-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

생성물 1

HCID 866124154-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (52 mg, 0.05 mmol) was dissolved in 8 ml toluene. 4-Chloro-7-iodo-2-methyl-thiazolo[4,5-c]pyridine (280 mg, 0.90 mmol) (Example B), 3-pyridineboronic acid (133 mg, 1.08 mmol), 2M sodium carbonate (2.70 ml, 5.4 mmol) and 2 ml ethanol were added and the mixture stirred at 80° C. for 6 hrs. The reaction mixture was extracted with water and two times ethyl acetate. The organic extracts were washed with water and brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 9:1->0:100 gradient). The desired compound was obtained as a light yellow solid (100 mg, 42%), MS: m/e=263.1 (M+H+).

후처리

  1. extractionThe reaction mixture was extracted with water and two times ethyl acetate
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 9:1->0:100 gradient)

출처 및 근거

ORD 기록
ord-0bc404bf89b5471684ed443d92501cf1
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659401B2

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