Acetonitrile → 2-[(2-{2-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenoxy}ethyl)amino]ethanol

HRID 2364959ノート

反応式

HRID 2364959 の反応式
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[S:14][CH:15]=1.FC(F)(F)C1SC=C([C:27]2C=CC=C[C:28]=2[OH:33])N=1.BrCCBr.C(#[N:42])C>>[F:17][C:16]([F:19])([F:18])[C:13]1[S:14][CH:15]=[C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH2:2][NH:42][CH2:27][CH2:28][OH:33])[N:12]=1

参加物

5

反応物 4

HCID 6342AcetonitrileHCID 78391,2-DibromoethaneHCID 683799052-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenolHCID 68380402Thiazole, 4-[2-(2-bromoethoxy)phenyl]-2-(trifluoromethyl)-

生成物 1

HCID 683801062-[(2-{2-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenoxy}ethyl)amino]ethanol

反応条件

温度
70 °C

実験手順

Synthesis of 4-[2-(2-bromoethoxy)phenyl]-2-(trifluoromethyl)-1,3-thiazole (C5) Cesium carbonate (266 mg, 0.816 mmol) was added to a solution of 2-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenol (C4) (100 mg, 0.408 mmol) and 1,2-dibromoethane (0.35 mL, 4.1 mmol) in acetonitrile (33 mL), and the mixture was heated at 70° C. for 18 hours. After cooling to room temperature, the reaction was partitioned between dichloromethane and water; the organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane) afforded the title compound. Yield: 115 mg, 0.327 mmol, 80%. 1H NMR (400 MHz, CDCl3) δ 3.78 (br dd, J=5.5, 5.5 Hz, 2H), 4.48 (dd, J=5.7, 5.5 Hz, 2H), 6.97 (br d, J=8.4 Hz, 1H), 7.13 (ddd, J=7.7, 7.4, 1.1 Hz, 1H), 7.35 (ddd, J=8.3, 7.3, 1.8 Hz, 1H), 8.31 (dd, J=7.8, 1.8 Hz, 1H), 8.37 (s, 1H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was partitioned between dichloromethane and water
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-2220b755d76f450dae8177de7a461ee1
出典データセット
uspto-grants-2014_04
特許番号
US08697673B2

反応ノート

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