Diethyl[(5-methoxy-6-nitropyridin-3-yl)methyl]phosphonate → Diethyl[(6-amino-5-methoxypyridin-3-yl)methyl]phosphonate

HRID 1948120

반응식

HRID 1948120 반응식
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([N+:18]([O-])=O)=[C:14]([O:16][CH3:17])[CH:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([NH2:18])=[C:14]([O:16][CH3:17])[CH:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

참가 물질

4

반응물 1

HCID 86654066Diethyl[(5-methoxy-6-nitropyridin-3-yl)methyl]phosphonate2회

생성물 1

HCID 86654065Diethyl[(6-amino-5-methoxypyridin-3-yl)methyl]phosphonate수율 92%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

Diethyl[(5-methoxy-6-nitropyridin-3-yl)methyl]phosphonate (Compound 308B, 102.6 mg) was hydrogenated in the presence of 10% Pd/C (20 mg) in MeOH (5 mL) under 1 atmosphere for 4 h. The catalyst was filtered off, the filtrate was concentrated, and the residue (85 mg, 92% yield) was used in the next step without purification. 1H NMR (CDCl3, 400 MHz): δ=1.27 (dt, J=2.0, 6.8 Hz, 6H), 3.02 (d, J=20.8 Hz, 2H), 3.84 (s, 3H), 4.01-4.08 (m, 4H), 4.74 (s, 2H), 6.98 (t, J=2.0 Hz, 1H), 7.52 (t, J=2.0 Hz, 1H). MS (ES+): m/z 275.10 [MH+]. HPLC: tR=0.77 min (UPLC TOF, polar—3 min).

후처리

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-e28c9562b0434905a30f5ff4fb35dd27
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399433B2

연결된 노트

불러오는 중…