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

HRID 511548

반응식

HRID 511548 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH:6]=[N:7][C:8]=1[N+:9]([O-])=O>CO.[Pd]>[NH2:9][C:8]1[N:7]=[CH:6][C:5]([CH2:12][P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])=[CH:4][C:3]=1[O:2][CH3:1]

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, 6 H), 3.02 (d, J=20.8 Hz, 2 H), 3.84 (s, 3 H), 4.01-4.08 (m, 4 H), 4.74 (s, 2H), 6.98 (t, J=2.0 Hz, 1 H), 7.52 (t, J=2.0 Hz, 1 H). 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-4a73d22e762f4ff39dab914e675fa381
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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