Dichloromethane → 3-Chloro-N-{6-methyl-3-[3-(methyloxy)phenyl]-2-phenylthieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

HRID 573622노트

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HRID 573622 반응식
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53250396N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

생성물 1

HCID 683241493-Chloro-N-{6-methyl-3-[3-(methyloxy)phenyl]-2-phenylthieno[2,3-b]pyridin-4-yl}-benzenesulfonamide수율 56.6%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (50 mg, 0.095 mmol) (Example 33), phenylboronic acid (13.97 mg, 0.115 mmol), sodium carbonate (20.23 mg, 0.191 mmol) and PdCl2(dppf).DCM (3.90 mg, 4.77 μmol) in DMF (1 mL) and water (250 μl) was heated at 90° C. under nitrogen, for 3.5 h. The reaction mixture was then cooled to RT and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in DCM, afforded the title compound (28 mg). LCMS (A) m/z: 521 [M+1]+, Rt 1.57 min (acidic), Rt 0.98 min (basic).

후처리

  1. concentrationconcentrated
  2. customPurification by chromatography on silica gel
  3. washeluting with a gradient of 0-20% ethyl acetate in DCM

출처 및 근거

ORD 기록
ord-48bfe2d2e7374c748054cfe2268fb855
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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