Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 2283473노트

반응식

HRID 2283473 반응식
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([I:19])=[CH:4][N:3]=1.[CH3:20]I>C(Cl)(Cl)Cl>[I:19][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([O:1][CH3:20])=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 178522276HCID 178522276, 화합물

생성물 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate수율 53.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of benzyl (2-hydroxy-5-iodopyridin-3-yl)carbamate (16 g, 43 mmol) in CHCl3 (250 mL) was added Ag2CO3 (16.1 g, 58.4 g) and methyl iodide (27.0 mL, 434 mmol) in the dark, and the mixture stirred at RT for overnight. The solid was removed by filtration and the solvent was concentrated and purified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate) to afford benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate (8.85 g, 53% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.61 (br, 1H), 7.98 (d, J=1.6 Hz, 1H), 7.35-7.42 (m, 5H), 7.12 (s, 1H), 5.21 (s, 2H), 3.95 (s, 3H); MS (ES) m/z 385 (M+H).

후처리

  1. customThe solid was removed by filtration
  2. concentrationthe solvent was concentrated
  3. custompurified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-954555dc8a2c48878e91d4c82f3d31e9
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145393B2

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