Sodium Carbonate → 5-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 985607ノート

反応式

HRID 985607 の反応式
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].[C:11]1(B(O)O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]([C:19]2[C:20]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1)=[O:4]

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 11773TriphenylarsineHCID 2545321-Naphthaleneboronic acidHCID 11600885Methyl 5-bromo-1H-pyrrole-2-carboxylate

生成物 1

HCID 697453065-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester収率 81.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Argon gas was bubbled 15 min through a solution of 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester (10.0 mmol, 2.04 g), 1-naphthylboronic acid (30.0 mmol, 5.16 g), 2M aqueous sodium carbonate (20 ml), and DMF (150 ml). The mixture was then treated with tris(dibenzylidienacetone)dipalladium (0) (0.50 mmol, 0.46 g), and triphenylarsine (2.0 mmol, 0.61 g), then heated to reflux under argon for 12 h. The mixture was partitioned between ethyl acetate (500 ml) and water (150 ml). The organics were filtered through celite, washed with brine (3×50 ml), then concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 2.05 g (81%) of 5-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) δ 9.37 (1H, s), 8.22-8.17 (1H, m), 8.16-7.89 (2H, m), 7.59-7.50 (4H, m), 7.88 (1H, dd, J=3.9, 2.7), 6.22 (1H, dd, J=3.8. 2.6), 3.88 (3H, s).

後処理

  1. temperatureheated
  2. temperatureto reflux under argon for 12 h
  3. customThe mixture was partitioned between ethyl acetate (500 ml) and water (150 ml)
  4. filtrationThe organics were filtered through celite
  5. washwashed with brine (3×50 ml)
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-f8078f23463945e28cd9f5e83af2b2d9
出典データセット
uspto-grants-2005_03
特許番号
US06872745B2

反応ノート

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