5-Bromo-3-pyridinecarboxaldehyde → (4R,5R)-4-(5-Bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

HRID 2362345Notes

Reaction equation

HRID 2362345 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][C:10](=[O:19])[NH:9]2)[CH:5]=CN=1.[F:20]C1C=C(C=CC=1)CP(=O)(OCC)OCC.BrC1C=[N:39][CH:40]=C(C=1)C=O>>[Br:1][C:2]1[CH:7]=[C:6]([C@@H:8]2[C@@H:12]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[O:11][C:10](=[O:19])[NH:9]2)[CH:5]=[N:39][CH:40]=1

Participants

4

Reactant 3

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 11311157Diethyl 3-fluorobenzylphosphonateHCID 86673413(4R,5R)-4-(2-Bromopyridin-4-yl)-5-phenyloxazolidin-2-one

Product 1

HCID 69084164(4R,5R)-4-(5-Bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

Procedure

Prepared according to the same procedure as (4R,5R)-4-(2-bromopyridin-4-yl)-5-phenyloxazolidin-2-one, starting with diethyl 3-fluorobenzylphosphonate and 5-bromonicotinaldehyde. 1H-NMR (CDCl3, 500 MHz) δ 8.72 (d, J=2.1, 1H), 8.41 (d, J=1.8, 1H), 7.94 (dd, J=2.1, 1.8, 1H), 7.42 (ddd, J=7.9, 7.9, 5.8, 1H), 7.14 (ddd, J=8.6, 8.6, 2.4, 1H), 7.01-7.10 (m, 2H), 6.78 (bs, 1H), 5.27 (d, J=7.3, 1H), 4.81 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 163.2 (d, J=249), 158.5, 152.0, 146.4, 138.5 (d, J=6.7), 136.7, 135.7, 131.1 (d, J=8.6), 121.6 (d, J=17), 116.8 (d, J=21), 113.0 (d, J=22), 84.8, 62.2. Mass spec.: 337.06 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-882a29fcd42848b28ff863a8ee53b56a
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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