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

HRID 1443083ノート

反応式

HRID 1443083 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-0bc404bf89b5471684ed443d92501cf1
出典データセット
uspto-grants-2010_02
特許番号
US07659401B2

反応ノート

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