1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66960678、化合物

HRID 69037ノート

反応式

HRID 69037 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]2.Br[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([O:29][CH3:30])=[N:21][CH:20]=1.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.CC(C)([O-])C.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.O1CCOCC1>[CH3:30][O:29][C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]3)=[CH:20][N:21]=1

参加物

8

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 247666564-Bromo-1-methoxyisoquinolineHCID 669605486-(3-aminopropoxy)-1-methyl-1H-quinolin-2-one

生成物 1

HCID 66960678HCID 66960678、化合物収率 25.5%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

6-(3-Amino-propoxy)-1-methyl-1H-quinolin-2-one (232 mg), 4-bromo-1-methoxy-isoquinoline (286 mg), palladium acetate (II) (22 mg), xantphos (558 mg), and sodium t-butoxide (192 mg) were added to dioxane (10 ml). The mixture was heated at 80° C. for overnight under argon atmosphere. The reaction liquid was cooled to room temperature. Water was added to the reaction mixture, and followed by celite filtration. The filtrate was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→1:0). The purified product was condensed under reduced pressure to give the title compound (99 mg) as a brown amorphous solid.

後処理

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. filtrationfollowed by celite filtration
  4. extractionThe filtrate was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→1:0)
  8. customcondensed under reduced pressure

出典と根拠

ORDレコード
ord-425bd318639b4230977bf145bb7dda04
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

反応ノート

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