2-(Propane-2-sulfonyl)aniline → Methyl 4'-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)pyridin-2-ylamino)-5'-methoxy-2'-methylbiphenyl-4-carboxylate

HRID 388578

반응식

HRID 388578 반응식
Br[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=3)=[C:12]([CH3:28])[CH:11]=2)[CH:3]=1.[CH:29]([S:32]([C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[NH2:37])(=[O:34])=[O:33])([CH3:31])[CH3:30].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.CC(C)([O-])C.[Na+]>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].C1COCC1>[Cl:8][C:7]1[C:2]([NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=2[S:32]([CH:29]([CH3:31])[CH3:30])(=[O:34])=[O:33])=[CH:3][C:4]([NH:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=3)=[C:12]([CH3:28])[CH:11]=2)=[N:5][CH:6]=1

참가 물질

7

반응물 4

HCID 126463662-(Propane-2-sulfonyl)anilineHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 23676156Sodium t-butoxideHCID 59764478Methyl 4'-(4-bromo-5-chloropyridin-2-ylamino)-5'-methoxy-2'-methylbiphenyl-4-carboxylate

생성물 1

HCID 59764572Methyl 4'-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)pyridin-2-ylamino)-5'-methoxy-2'-methylbiphenyl-4-carboxylate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

Methyl 4′-(4-bromo-5-chloropyridin-2-ylamino)-5′-methoxy-2′-methylbiphenyl-4-carboxylate generated in Step 2 (9 mg, 0.022 mmol), 2-(isopropylsulfonyl)aniline (4 mg, 0.022 mmol, 1 equiv), Pd2(dba)3 (1.7 mg, 0.002 mmol, 0.1 equiv.), 2-(Dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (1.8 mg, 0.004 mmol, 0.2 equiv.), and Sodium tert-butoxide (2.7 mg, 0.028 mmol, 1.3 equiv.) are added to THF (1 mL). The resulting mixture is bubbled with N2 gas for 5 minutes and then heated at 150° C. for 4 hours. After cooling to room temperature, the reaction mixture is diluted into EtOAc and washed with H2O. The EtOAc layer is dried over Mg2SO4 and concentrated in vacuo. Silica gel chromatography (hexanes-EtOAc) affords Methyl 4′-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)pyridin-2-ylamino)-5′-methoxy-2′-methylbiphenyl-4-carboxylate (254); MS m/z 580.2 (M+1).

후처리

  1. customThe resulting mixture is bubbled with N2 gas for 5 minutes
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction mixture is diluted into EtOAc
  4. washwashed with H2O
  5. dry with materialThe EtOAc layer is dried over Mg2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-05174795088b4049919cc2ddea537768
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377921B2

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