Methyl Anthranilate → methyl 2-(9H-carbazol-1-ylamino)benzoate

HRID 531899

反応式

HRID 531899 の反応式
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Br[C:13]1[C:25]2[NH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:22]1([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([O:10][CH3:11])=[O:9])[C:23]2[NH:24][C:25]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 8635Methyl AnthranilateHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 112303351-Bromo-9H-carbazole

生成物 1

HCID 68242730methyl 2-(9H-carbazol-1-ylamino)benzoate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

35.51 g (234.9 mmol) of methyl anthranilate are dissolved in 500 ml of toluene and degassed well. 52 g (213 mmol) of 1-bromocarbazole, 2.1 g (10.7 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1.19 g (5.34 mmol) of Pd(OAc)2 and 76.5 g (234.9 mmol) of Cs2CO3 are added, and the mixture is then degassed and stirred at 100° C. under a protective-gas atmosphere for 24 h. The solids are subsequently filtered off via Celite, and the organic phase is washed with water, dried over MgSO4 and evaporated. The crude product is washed by stirring with hot heptane, giving 57.4 g (108 mmol), 86% of theory, purity according to HPLC 86%.

後処理

  1. customdegassed well
  2. customthe mixture is then degassed
  3. filtrationThe solids are subsequently filtered off via Celite
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. washThe crude product is washed
  8. stirringby stirring with hot heptane
  9. customgiving 57.4 g (108 mmol), 86% of theory, purity

出典と根拠

ORDレコード
ord-de53838ceb6f4bbcabb63ac118599e64
出典データセット
uspto-grants-2016_05
特許番号
US09356243B2

関連ノート

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