Toluene → 2-Bromo-6-(2-pyridin-3-yl-thiazol-5-yl)-pyridine

HRID 1854620ノート

反応式

HRID 1854620 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[S:18][C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:16][CH:15]=1)CCC.C(Cl)Cl.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.O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:14]2[S:18][C:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:16][CH:15]=2)[N:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 122742,6-DibromopyridineHCID 673254043-(5-Tributylstannanyl-thiazol-2-yl)-pyridine

生成物 1

HCID 533113132-Bromo-6-(2-pyridin-3-yl-thiazol-5-yl)-pyridine収率 35%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

A sealed tube was charged with 2,6-dibromopyridine (269 mg, 1.13 mmol), 3-(5-tributylstannanyl-thiazol-2-yl)-pyridine (511 mg, 1.13 mmol), Pd(PPh3)4 (131 mg, 0.11 mmol), [1,1-Bis(diphenylphosphino)ferrocene]palladium(II) chloride. CH2Cl2 (20 mg, 0.024 mmol) and anhydrous and degassed toluene (5 ml) and heated to 110° C. with stirring for 36 h. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®, eluting with cyclohexane/ethyl acetate to afford the title compound as a white solid (125 mg, 35%). 1H NMR (DMSO-d6, 300 MHz): δ=9.21 (d, J=1.7 Hz, 1H), 8.72 (s, 1H), 8.70 (m, 1H), 8.39 (m, 1H), 8.14 (d, J=7.8 Hz, 1H), 7.88 (dd, J=8.0; 7.8 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.57 (m, 1H).

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®
  7. washeluting with cyclohexane/ethyl acetate

出典と根拠

ORDレコード
ord-e66f448996fb4263bc92e301dadb0978
出典データセット
uspto-grants-2015_02
特許番号
US08962665B2

反応ノート

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