2-(Tributylstannyl)pyridine → 4-Chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine

HRID 1431706ノート

反応式

HRID 1431706 の反応式
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCCC[Sn]([C:27]1[N:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(CCCC)CCCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][N:32]=2)[C:11]=1[CH3:12]

参加物

5

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 220826612,4-Dichloro-3-methyl-1,8-naphthyridine

生成物 1

HCID 596310684-Chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

The Stille coupled product was prepared according to Procedure E using 2,4-dichloro-3-methyl-1,8-naphthyridine (540 mg, 2.53 mmol), 2-(1,1,1-tributylstannyl)pyridine (933 μL, 2.53 mmol), Pd(PPh3)4 in toluene (10 mL) and heating at reflux for 14 h. The reaction was allowed to cool to rt and evaporated in vacuo. The resulting residue was triturated with hexanes and the solid was dried under vacuum to give 4-chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine. 1H NMR (400 MHz, CDCl3) δ ppm 9.14 (1H, dd, J=4.3, 2.0 Hz), 8.72 (1H, ddd, J=4.9, 1.8, 1.0 Hz), 8.65 (1H, dd, J=8.3, 1.9 Hz), 8.09 (1H, dt, J=8.0, 1.1 Hz), 7.90 (1H, td, J=7.7, 1.8 Hz), 7.60 (1H, dd, J=8.3, 4.2 Hz), 7.40 (1H, ddd, J=7.6, 4.8, 1.3 Hz), 2.75 (3H, s)

後処理

  1. customwas prepared
  2. temperatureheating
  3. temperatureat reflux for 14 h
  4. customevaporated in vacuo
  5. customThe resulting residue was triturated with hexanes
  6. customthe solid was dried under vacuum

出典と根拠

ORDレコード
ord-743fda19ca1348db856aaaba8ef4611c
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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