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

HRID 511356Notes

Reaction equation

HRID 511356 reaction equation
NC1C=CC(F)=CC=1C(NC)=O.[F:13][C:14]1[C:28]([O:29][CH3:30])=[C:27]([N+:31]([O-])=O)[CH:26]=[CH:25][C:15]=1[CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>>[NH2:31][C:27]1[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[C:14]([F:13])[C:28]=1[O:29][CH3:30]

Participants

3

Reactant 2

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 86654025Diethyl (2-fluoro-3-methoxy-4-nitrobenzyl)phosphonate2×

Product 1

HCID 86654024Diethyl (4-amino-2-fluoro-3-methoxybenzyl)phosphonate

Procedure

The title compound was prepared using the procedure from Compound 102A (2-Amino-5-fluoro-N-methylbenzamide) with Diethyl (2-fluoro-3-methoxy-4-nitrobenzyl)phosphonate (Compound 147B). 1H NMR (CDCl3, 400 MHz): δ=1.29 (t, J=6.95 Hz, 6 H), 3.13-3.21 (m, 2 H), 3.93 (d, J=1.52 Hz, 3 H), 4.04-4.12 (m, 4 H), 6.55 (d, J=8.34 Hz, 1 H), 6.83 (td, J=7.96, 2.78 Hz, 1 H). MS (ES+): m/z 292.11 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-fe2fbfba9d264d8da4bc1b47c10ace23
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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