Potassium Phosphate, Tribasic → 6-(benzylthio)-1-(2-bromo-4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

HRID 1504410

반응식

HRID 1504410 반응식
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:43][C:44]1[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[CH:46][C:45]=1I.[NH2:55][C:56]1[CH:61]=[CH:60][C:59]([S:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)=[CH:58][C:57]=1/[CH:70]=[CH:71]/[C:72]([O:74]CC)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:63]([S:62][C:59]1[CH:58]=[C:57]2[C:56](=[CH:61][CH:60]=1)[N:55]([C:45]1[CH:46]=[CH:47][C:48]([C:50]([F:53])([F:52])[F:51])=[CH:49][C:44]=1[Br:43])[C:72](=[O:74])[CH:71]=[CH:70]2)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 117740420(E)-Ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate

생성물 1

HCID 1177371566-(benzylthio)-1-(2-bromo-4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of xantphos (0.277 g, 0.479 mmol), Pd2(dba)3 (0.146 g, 0.160 mmol), 2-bromo-1-iodo-4-(trifluoromethyl)benzene (Oakwood Chemical, 1.232 g, 3.51 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (1.000 g, 3.19 mmol), and potassium phosphate (2.032 g, 9.57 mmol) in 10 mL dioxane was heated to 90° C. for 5 hours. The reaction mixture was diluted with water and extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was used in the next step without purification. m/z (ESI) 536.0 (M+H)+.

후처리

  1. extractionextracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was used in the next step without purification

출처 및 근거

ORD 기록
ord-adde6805a2f240528c0b58d70b40fcf3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212182B2

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