2-Amino-5-fluoro-N-methylbenzamide → Diethyl (4-amino-3-fluoro-5-methoxybenzyl)phosphonate

HRID 511348Notes

Reaction equation

HRID 511348 reaction equation
NC1C=CC(F)=CC=1C(NC)=O.[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[C:27]([O:32][CH3:33])[C:28]=1[N+:29]([O-])=O)[CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>>[NH2:29][C:28]1[C:27]([O:32][CH3:33])=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=1[F:13]

Participants

3

Reactant 2

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 86654023Diethyl (3-fluoro-5-methoxy-4-nitrobenzyl)phosphonate2×

Product 1

HCID 86654022Diethyl (4-amino-3-fluoro-5-methoxybenzyl)phosphonate

Procedure

The title compound was prepared using the procedure from Compound 102A (2-Amino-5-fluoro-N-methylbenzamide) with Diethyl (3-fluoro-5-methoxy-4-nitrobenzyl)phosphonate (Compound 146B). 1H NMR (CDCl3, 400 MHz): δ=1.27 (t, J=7.07 Hz, 6 H), 2.99-3.08 (m, 2H), 3.87 (s, 3 H), 4.00-4.06 (m, 4 H), 6.59 (s, 1 H), 6.63 (dt, J=10.74, 2.21 Hz, 1 H). MS (ES+): m/z 292.06 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-561bb9faacd844bbb917ff563ab689bc
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…