3-Chloro-6-methylpyridazine → 2-(6-Methylpyridazin-3-ylamino)dibenzothiophene

HRID 1064013

반응식

HRID 1064013 반응식
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.Cl[C:16]1[N:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.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]>[CH3:22][C:19]1[N:18]=[N:17][C:16]([NH:1][C:2]2[CH:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 3

HCID 2272543-Chloro-6-methylpyridazineHCID 2984422-DibenzothiophenamineHCID 23676156Sodium t-butoxide

생성물 1

HCID 222777962-(6-Methylpyridazin-3-ylamino)dibenzothiophene수율 34.7%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-aminodibenzothiophene (0.90 g, 4.52 mM), 3-chloro-6-methyl-pyridazine (0.58 g, 4.52 mM), sodium t-butoxide (0.61 g, 6.33 mM), tris(dibenzylidene-acetone)dipalladium(0) (0.083 g, 0.09 mM) and S-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.113 g, 0.18 mM) in toluene (23 ml) was heated to 80° C. for 18 hours under an inert atmosphere. On cooling to room temperature the mixture was diluted with DCM, washed with aqueous potassium carbonate, dried over sodium sulphate and concentrated. Chromatography (eluent gradient of DCM to EtOAc then MeOH:EtOAc (1:9)) gave the product as an off white solid (0.456 g). NMR: 9.38 (brs, 1H), 8.81 (brs, 1H), 8.18 (m, 1H), 8.01 (m, 1H), 7.94 (d, 1H), 7.75 (dd, 1H), 7.50 (m, 1H), 7.36 (d, 1H), 7.14 (d, 1H), 2.50 (s, 3H); m/z 292.29.

후처리

  1. temperatureOn cooling to room temperature the mixture
  2. washwashed with aqueous potassium carbonate
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9559bbad7a0d43079c2afd368f2ac88f
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967216B2

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