HCID 21942616、化合物 → HCID 11021991、化合物

HRID 2216897ノート

反応式

HRID 2216897 の反応式
C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][N:4]=1.Br[C:14]1[O:18][C:17]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:16][CH:15]=1>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>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:14]2[O:18][C:17]([C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])=[CH:16][CH:15]=2)=[N:4][CH:5]=1)#[N:10]

参加物

5

反応物 2

HCID 21942616HCID 21942616、化合物HCID 219426553-(5-Bromofuran-2-yl)-benzonitrile

生成物 1

HCID 11021991HCID 11021991、化合物収率 23%

試薬・触媒・溶媒 2

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

反応条件

温度
110 °C

実験手順

In a similar fashion, Pd(PPh3)4 (10 mg, 0.009 mmol) was added to a solution of 2-trimethylstannyl-5-cyano-pyridine (22.7 mg, 0.085-mmol) and 3-(5-bromofuran-2-yl)-benzonitrile (31 mg, 0.125 mmol) in toluene (1 mL) under argon. The resulting solution was stirred at 110° C. for 15 h. After cooling to room temperature, the solvent was removed in vacuo. Chromatography (5 g silica gel SPE tube, 50% chloroform in hexane to 20% ethyl acetate in 1:1 chloroform:hexane) followed by triturating with 50% dichloromethane in hexane afforded 5.3 mg (23%) of 3-(5-(5-cyano-2-pyridyl)-2-furyl)-benzonitrile (91% pure by GC/MS, contaminated by 9% dimer). 1H-NMR (CDCl3), δ (ppm): 8.85 (s, 1H), 7.87–8.05 (m, 5H), 7.52–7.63 (m, 3H), 7.36 (d, 1H), 6.95 (d, 1H), dimer impurity caused peak intensity to increase in region 8.00, 7.92, 7.49–7.57, plus 2 peaks additional peaks exactly overlapping with pure dimer @ δ (ppm): 6.87 (d) & 6.80 d).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed in vacuo
  3. customby triturating with 50% dichloromethane in hexane

出典と根拠

ORDレコード
ord-eb98a54b6b3943639ae011ef9b9e4014
出典データセット
uspto-grants-2006_09
特許番号
US07112595B2

反応ノート

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