Cesium fluoride → 6'-Methyl-2,3'-bipyridine-2'-carbonitrile

HRID 61092

反応式

HRID 61092 の反応式
Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)CCC.[F-].[Cs+]>CN(C=O)C.[Cu]I.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>[CH3:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:7][CH:6]=1

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 219527473-Bromo-6-methylpyridine-2-carbonitrile

生成物 1

HCID 593637166'-Methyl-2,3'-bipyridine-2'-carbonitrile収率 88%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3-bromo-6-methylpicolinonitrile (1 g, 5.1 mmol), 2-(tributylstannyl)pyridine (2.43 ml, 6.60 mmol), cesium fluoride (150 mg, 10.2 mmol), CuI (193 mg, 1.02 mmol) and Pd(PPh3)4 (586 mg, 0.51 mmol) in DMF (10 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a brown oil (0.87 g, 88%). MS (ESI) 196 (M+H).

後処理

  1. customwas degassed
  2. customThe solvent was removed in vacuo
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

出典と根拠

ORDレコード
ord-ca8ed7fd06cf4ff3a8a7b5ac5854dc1b
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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