3-Bromobenzonitrile → 3-pyrrolidin-1-ylbenzonitrile

HRID 1167301ノート

反応式

HRID 1167301 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[NH:62]1[CH2:66][CH2:65][CH2:64][CH2:63]1>O1CCCC1.C(OCC)C.O>[N:62]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH2:66][CH2:65][CH2:64][CH2:63]1

参加物

8

反応物 4

HCID 233813-BromobenzonitrileHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 71623323-pyrrolidin-1-ylbenzonitrile収率 5.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A reaction mixture of 3-bromo-benzonitrile (0.91 g, 5 mmol), tris(dibenzylidenecetone)-dipalladium (229 mg), (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (311 mg, 0.5 mmol), sodium tert-butoxide (740 mg, 7.7 mmol), pyrrolidine (0.58 mL, 6.9 mmol) in tetrahydrofuran (10 mL) was heated at 80° C. in a sealed tube for 6 h. The reaction mixture was worked up with water and diethyl ether. The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% ethyl acetate in hexanes yielded 3-pyrrolidin-1-yl-benzonitrile (45 mg, 5%).

後処理

  1. washThe organic layers were washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe solid was then filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  6. washeluting with 0-5% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-50de50b618b444b6936f0c49cef43f12
出典データセット
uspto-grants-2003_09
特許番号
US06617346B1

反応ノート

読み込み中…