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

HRID 573622ノート

反応式

HRID 573622 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-48bfe2d2e7374c748054cfe2268fb855
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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