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

HRID 397953노트

반응식

HRID 397953 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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) δ9.37 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-933704a5b36347b8ad3ad513da45eae1
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610730B2

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