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

HRID 531899

반응식

HRID 531899 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-de53838ceb6f4bbcabb63ac118599e64
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09356243B2

연결된 노트

불러오는 중…