6-Bromopyridine-2-carbaldehyde → (4R,5R)-4-(6-bromopyridin-2-yl)-5-(4-fluorophenyl)oxazolidin-2-one

HRID 2362358Notes

Reaction equation

HRID 2362358 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](OC)[CH:14]=3)[O:11][C:10](=[O:21])[NH:9]2)C=N[CH:7]=1.[Br:22][C:23]1[N:28]=C(C=O)C=CC=1.[F:31]C1C=CC(CP(=O)(OCC)OCC)=CC=1>>[Br:22][C:23]1[N:28]=[C:4]([C@@H:8]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([F:31])=[CH:17][CH:18]=3)[O:11][C:10](=[O:21])[NH:9]2)[CH:3]=[CH:2][CH:7]=1

Participants

4

Reactant 3

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 11064685Diethyl P-((4-fluorophenyl)methyl)phosphonateHCID 69086194(4R,5R)-4-(5-bromopyridin-3-yl)-5-(3-methoxyphenyl)oxazolidin-2-one

Product 1

HCID 86673415(4R,5R)-4-(6-bromopyridin-2-yl)-5-(4-fluorophenyl)oxazolidin-2-one

Procedure

Prepared according to the same procedure as optically-enriched (4R,5R)-4-(5-bromopyridin-3-yl)-5-(3-methoxyphenyl)oxazolidin-2-one, starting with 6-bromopicolinaldehyde and diethyl 4-fluorobenzylphosphonate. 1H-NMR (CDCl3, 500 MHz) δ 7.65 (dd, J=7.9, 7.6, 1H), 7.51 (d, J=7.6, 1H), 7.46 (dd, J=8.9, 5.2, 2H), 7.41 (d, J=7.6, 1H), 7.13 (m, 3H), 5.61 (d, J=7.5, 1H), 4.90 (d, J=5.8, 1H). 13C-NMR (CDCl3, 126 MHz) δ 163.1 (d, J=249), 159.4 (d, J=55), 142.6, 139.8, 134.0, 128.3, 127.8, 127.7, 119.6, 116.2, 116.0, 83.1, 64.4.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8c81726732a1431a8a0201309860a465
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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