4-(4-Bromophenyl)-1,3-thiazol-2-amine → Methyl N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3,3,3-trifluoroalaninate

HRID 1436392노트

반응식

HRID 1436392 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH2:13])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16](=[O:23])[C:17]([C:19]([F:22])([F:21])[F:20])=O.C([BH3-])#N.[Na+]>C(Cl)Cl.CO.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([NH:13][C@H:17]([C:16]([O:15][CH3:14])=[O:23])[C:19]([F:22])([F:21])[F:20])[S:11][CH:12]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 6206834-(4-Bromophenyl)-1,3-thiazol-2-amineHCID 2734931Methyl 3,3,3-trifluoro-2-oxopropanoateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 86618600Methyl N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3,3,3-trifluoroalaninate수율 44%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

4-(4-Bromophenyl)-1,3-thiazol-2-ylamine (510 mg, 2.0 mmol) and methyl-3,3,3-trifluoropyruvate (0.10 mL, 1.0 mmol) were dissolved in 50 mL methylene chloride. Titanium (IV) chloride (1M in toluene, 1.6 mL, 1.6 mmol) was added dropwise to give an orange-brown suspension. The mixture was stirred for 15 min and then added by cannula to a solution of sodium cyanoborohydride (0.26 g, 3.0 mmol) in 50 mL of methanol. The mixture was stirred for 15 min and then quenched by the addition of H2O and saturated aqueous sodium bicarbonate. The mixture was extracted three times with methylene chloride. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (100% methylene chloride) afforded methyl N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3,3,3-trifluoroalaninate (0.17 g, 44%) as a white solid. MS (ES) m/z 392.8.

후처리

  1. customto give an orange-brown suspension
  2. stirringThe mixture was stirred for 15 min
  3. customquenched by the addition of H2O and saturated aqueous sodium bicarbonate
  4. extractionThe mixture was extracted three times with methylene chloride
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fb8315d3e04f4b7ca6e7ccf310ca097c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618990B2

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