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

HRID 1064013

反応式

HRID 1064013 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 222777962-(6-Methylpyridazin-3-ylamino)dibenzothiophene収率 34.7%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9559bbad7a0d43079c2afd368f2ac88f
出典データセット
uspto-grants-2005_11
特許番号
US06967216B2

関連ノート

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