Sodium Carbonate → HCID 57774343, 화합물

HRID 1786763노트

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HRID 1786763 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 57774343HCID 57774343, 화합물수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e1735d1e75c74ebb9fa2d2666c3cd572
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507826B2

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