Dimethyl nitromalonate → Methyl 4-propyl-5-(pyridine-2-yl)isoxazole-3-carboxylate

HRID 1951941

反応式

HRID 1951941 の反応式
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)#[C:2][CH2:3][CH2:4][CH3:5].[N+:12]([CH:15](C(OC)=O)[C:16]([O:18][CH3:19])=[O:17])([O-])=[O:13].F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC>C1(C)C=CC=CC=1>[CH2:3]([C:2]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:12][O:13][C:1]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:4][CH3:5]

参加物

5

反応物 3

HCID 226085Dimethyl nitromalonateHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphateHCID 110947572-(Pent-1-ynyl)pyridine

生成物 1

HCID 58062816Methyl 4-propyl-5-(pyridine-2-yl)isoxazole-3-carboxylate収率 5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 2-(pent-1-ynyl)pyridine (150 mg, 1.03 mmol), dimethyl nitromalonate (0.35 mL, 2.58 mmol), and 1-butyl-3-methylimidazolium hexafluorophosphate (0.021 mL, 0.103 mmol) in toluene (3 mL) was heated to 170° C. for 120 minutes under microwave. The reaction mixture was concentrated to yield a crude product which was purified by silica gel chromatography with hexanes/ethyl acetate (10/1) to afford methyl 4-propyl-5-(pyridine-2-yl)isoxazole-3-carboxylate (14.3 mg, 0.052 mmol). The compound had an HPLC retention time=3.05 min.—Column: YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH—90% Water—0.2% H3PO4; Solvent B=90% MeOH—10% water—0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=247.1. 1H NMR (500 MHz, CDCl3) δ ppm 0.97 (t, 3H), 1.66 (sxt, J=7.48 Hz, 2H), 3.15-3.20 (m, 2H), 4.01 (s, 3H), 7.33 (ddd, J=7.56, 4.81, 1.10 Hz, 1H), 7.83 (td, J=7.77, 1.79 Hz, 1H), 7.91 (d, J=7.97 Hz, 1H), and 8.72 (d, J=4.12 Hz, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto yield a crude product which
  3. customwas purified by silica gel chromatography with hexanes/ethyl acetate (10/1)

出典と根拠

ORDレコード
ord-966d7f9c96574b0ba9f4eb503f73830d
出典データセット
uspto-grants-2013_03
特許番号
US08404672B2

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