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

HRID 1504410

反応式

HRID 1504410 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-adde6805a2f240528c0b58d70b40fcf3
出典データセット
uspto-grants-2015_12
特許番号
US09212182B2

関連ノート

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