2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 1-(5-Chloro-benzo[1,3]dioxol-4-ylamino)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029152

반응식

HRID 1029152 반응식
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]2[O:22][CH2:23][O:24][C:20]=2[C:19]=1[NH2:27].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]2[O:22][CH2:23][O:24][C:20]=2[C:19]=1[NH:27][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2

참가 물질

8

반응물 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 23676156Sodium t-butoxideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

생성물 1

HCID 581683001-(5-Chloro-benzo[1,3]dioxol-4-ylamino)-5H-benzo[c][1,8]naphthyridin-6-one수율 76.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매HCID 22728543Water ethylacetate용매

반응 조건

온도
100 °C

실험 절차

Compound 83 (250 mg, 1.08 mmol), 5-chloro-benzo[1,3]dioxol-4-ylamine (279 mg, 1.63 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), X-Phos (52 mg, 0.11 mmol), and NaOtBu (312 mg, 3.25 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 188 (301 mg, 76% yield) as a white solid. LC-MS (M+H=366, obsd.=366).

후처리

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc/H2O
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-ff3094e82c84411fac9cd09cd3477029
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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