Cesium carbonate → 5-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

HRID 405833

반응식

HRID 405833 반응식
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][C:8]1[N:9]=[CH:10][NH:11][CH:12]=1.Br[C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1>[Cu]I.CN(C=O)C>[CH3:7][C:8]1[N:9]=[CH:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:12]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 706222-Amino-5-bromopyridineHCID 178418800HCID 178418800, 화합물

생성물 1

HCID 575128615-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

To a microwave tube with a magnetic stirring bar was charged CuI (382 mg, 2.0 mmol), Cs2CO3 (6.5 g, 20.0 mmol), 4-methyl-1H-imidazole (1.15 g, 14.0 mmol), 5-bromopyridin-2-amine (1.75 g, 10.0 mmol), and DMF (10 mL) under N2. The system was sealed and then evacuated twice and back filled with N2. The reaction mixture was stirred for 30 min at room temperature, and then heated at 120° C. for 48 h. The reaction mixture was then cooled to ambient temperature, diluted with 30 mL of ethyl acetate, washed with water. The combined organic layers were concentrated, and the resulting residue was purified by column chromatography on silica gel to provide 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (134). 1H NMR (400 MHz, d6-DMSO) δ 8.09 (m, 1H), 7.85 (d, J=1.6 Hz, 1H), 7.56 (dd, J=2.8, 8.8 Hz, 1H), 7.22 (t, J=1.2 Hz, 1H), 6.51 (dd, J=0.8, 8.8 Hz, 1H), 6.15 (s, 2H), 2.14 (d, J=1.2 Hz, 3H). MS m/z 175.1 (M+1)+.

후처리

  1. customThe system was sealed
  2. customevacuated twice
  3. additionback filled with N2
  4. temperatureheated at 120° C. for 48 h
  5. temperatureThe reaction mixture was then cooled to ambient temperature
  6. additiondiluted with 30 mL of ethyl acetate
  7. washwashed with water
  8. concentrationThe combined organic layers were concentrated
  9. customthe resulting residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-b5583c6589d54f36ab1a708aa4ca597c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754071B2

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