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碳酸钾 → 5-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde

HRID 1484792
笔记
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反应方程式

HRID 1484792 反应方程式
Br[CH2:2][C:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]=1[C:9]1[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=1.[OH:17][C:18]1[C:23]([CH:24]=[O:25])=[CH:22][C:21]([O:26][CH3:27])=[N:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[CH:14]([N:13]1[C:9]([C:4]2[CH2:5][O:6][CH2:7][CH2:8][C:3]=2[CH2:2][O:17][C:18]2[C:23]([CH:24]=[O:25])=[CH:22][C:21]([O:26][CH3:27])=[N:20][CH:19]=2)=[CH:10][CH:11]=[N:12]1)([CH3:16])[CH3:15]
参与物实验过程后处理来源与证据反应笔记

参与物

7

反应物 3

HCID 11430碳酸钾HCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeHCID 904080795-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole

产物 1

HCID 863040155-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde收率 38.3%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 6228N,N-二甲基甲酰胺溶剂
HCID 8857乙酸乙酯溶剂

实验过程

To a solution of 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole (50 mg, 0.19 mmol) (see the synthesis of Compound L) and 5-hydroxy-2-methoxyisonicotinaldehyde (30 mg, 0.23 mmol) in DMF (1 mL) was added K2CO3 (50 mg, 0.38 mmol). After stirred at room temperature for 3 h, it was diluted with water and EtOAc, organic layer was separated, and the aqueous layer was extracted with EtOAc, organic layer was combined, washed with brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=1:1) to give 5-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde (26 mg). 1H NMR (400 MHz, CDCl3) δ (ppm) 10.40 (s, 1H), 7.81 (s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.05 (s, 1H), 6.08 (d, J=1.6 Hz, 1H), 4.42 (s, 2H), 4.40 (m, 1H), 4.19 (s, 2H), 3.98 (t, J=5.6 Hz, 2H), 3.88 (s, 3H), 2.47 (s, 2H), 1.41 (d, J=6.8 Hz, 6H); MS (ESI) m/z 358.4 [M+H]+.

后处理

  1. customwas separated
  2. extractionthe aqueous layer was extracted with EtOAc, organic layer
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column (Hexanes/EtOAc=1:1)

来源与证据

ORD记录
ord-627f434c58f64021962a966f49aa77eb
来源数据集
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09422279B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记