Cesium carbonate → HCID 72950147, 화합물

HRID 517298

반응식

HRID 517298 반응식
Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:8]2(=[O:20])=[O:19])=[C:4]([F:23])[CH:3]=1.[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]1)(=[O:27])=[O:26].CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[F:23][C:4]1[CH:3]=[C:2]([O:34][CH:31]2[CH2:32][CH2:33][N:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:29][CH2:30]2)[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8]1(=[O:20])=[O:19]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 222729811-(Methanesulfonyl)piperidin-4-olHCID 867092782-[(4-Bromo-2-fluoro-phenyl)methyl]-6-phenyl-thiazinane 1,1-dioxide

생성물 1

HCID 72950147HCID 72950147, 화합물수율 40.4%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

반응 조건

온도
135 °C

실험 절차

2-(4-bromo-2-fluorobenzyl)-6-phenyl-1,2-thiazinane 1,1-dioxide (100 mg, 0.25 mmol), 1-methylsulfonylpiperidin-4-ol (67.2 mg, 0.38 mmol), copper(I) iodide (9.5 mg, 0.05 mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (24 mg, 0.1 mmol) and cesium carbonate (123 mg, 0.38 mmol) were weighed out in a vial and the vial was purged with nitrogen. p-Xylene (1 mL) was then added and the reaction was stirred at 135° C. for 16 hours. The reaction was then filtered through diatomaceous earth, concentrated and purified by reverse-phase HPLC to give 2-(2-fluoro-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzyl)-6-phenyl-1,2-thiazinane 1,1-dioxide (50.1 mg, 40% yield).

후처리

  1. customwas purged with nitrogen
  2. additionp-Xylene (1 mL) was then added
  3. filtrationThe reaction was then filtered through diatomaceous earth
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC

출처 및 근거

ORD 기록
ord-3063618d65d34c35bd51e10e34158eb5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115101B2

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