Sodium Carbonate → HCID 57774343、化合物

HRID 1024404ノート

反応式

HRID 1024404 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([Si:12]([C:17]#[CH:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:11]=[C:10]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[NH:8][C:5]2=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 637947(Triethylsilyl)acetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

生成物 1

HCID 57774343HCID 57774343、化合物収率 44%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 40 (9.5 g, 37.3 mmol) was dissolved in 320 mL of DMF and triethylsilylacetylene (20 mL, 112 mmol), Pd2Cl2 (dppf)2 (1.52 g, 1.9 mmol), lithium chloride (1.58 g, 37.3 mmol) and 2M Na2CO3 (7.9 mL, 74.7 mL) were added and the mixture was stirred and refluxed at 90° C. for 15 h under nitrogen. Diluted with ethyl acetate-ether mixture (1:1) and the organic phase washed with water and brine then dried (Na2SO4) and concentrated in vacuo. The residue was subjected to flash chromatography (20% EtOAc/80% hexanes) to give 4.37 g (44%) of the desired product 41. 1H NMR (500 MHz, CDCl3) 9.4 (bs, 1H), 8.2 (s, 1H), 7.9 (s, 1H), 6.6 (s, 1H), 0.9 (t, 9H), 0.75 (q, 6H).

後処理

  1. washthe organic phase washed with water and brine
  2. dry with materialthen dried (Na2SO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0bf79abcb7534ae896a7308674954e68
出典データセット
uspto-grants-2014_05
特許番号
US08722889B2

反応ノート

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