Benzophenone imine → 6-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine

HRID 1504771ノート

反応式

HRID 1504771 の反応式
CC(C)([O-])C.[Na+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24](Cl)[N:23]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:21][C:22]1[N:23]=[C:24]([N:20]=[C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:25]=[C:26]([CH3:28])[CH:27]=1

参加物

6

反応物 3

HCID 136809Benzophenone imineHCID 108989972,6-Dichloro-4-methylpyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 867316646-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

Toluene (27 mL), sodium tert-butoxide (0.925 g, 9.63 mmol), and benzophenone imine (1.75 g, 9.63 mmol) were added to 2,6-dichloro-4-methylpyridine (1.3 g, 8.0 mmol). The flask was purged with argon 3 times before 2-dicyclophenylphosphino-2′-(N,N-dimethylamino)biphenyl (0.474 g, 1.20 mmol) and Pd2(dba)3 (0.367 g, 0.401 mmol) were added. The flask was purged 3 times with argon, sealed, and heated to 80° C. After 16 hours, the reaction mixture was cooled to room temperature, diluted with water, and extracted with DCM. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-40% acetone/hexanes, linear gradient) to afford 6-chloro-N-(diphenylmethylidene)-4-methylpyridin-2-amine. 1H NMR (500 MHz, CDCl3) δ 7.83-7.73 (m, 2H), 7.49 (t, J=7.6 Hz, 2H), 7.44-7.34 (m, 2H), 7.34-7.27 (m, 2H), 7.21-7.12 (m, 2H), 6.72 (s, 1H), 6.27 (s, 1H), 2.15 (s, 3H).

後処理

  1. additionwere added
  2. customThe flask was purged 3 times with argon
  3. customsealed
  4. temperaturethe reaction mixture was cooled to room temperature
  5. additiondiluted with water
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (0-40% acetone/hexanes, linear gradient)

出典と根拠

ORDレコード
ord-201cd0aef27240b7a4b1a94c1e6a7676
出典データセット
uspto-grants-2015_12
特許番号
US09216173B2

反応ノート

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