2-Bromo-4-pyridinecarboxaldehyde → HCID 86673408, compound

HRID 2362337Notes

Reaction equation

HRID 2362337 reaction equation
BrC1N=C([C@@H]([NH:17][C:18](=[O:24])[O:19]C(C)(C)C)[C@H](O)C2C=CC=CC=2)C=CC=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][N:33]=1)[CH:29]=O.C([C:36](CC)(P(=O)([O-])[O-])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1)C>>[Br:25][C:26]1[CH:27]=[C:28]([C@@H:29]2[C@@H:36]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=3)[O:24][C:18](=[O:19])[NH:17]2)[CH:31]=[CH:32][N:33]=1

Participants

4

Reactant 3

HCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 86673407HCID 86673407, compoundHCID 86673409HCID 86673409, compound

Product 1

HCID 86673408HCID 86673408, compound

Procedure

Prepared according to the same procedure as (±)-tert-Butyl (1R,2R)-1-(6-bromopyridin-2-yl)-2-hydroxy-2-phenylethylcarbamate, starting with 2-bromoisonicotinaldehyde and diethyl-3-methoxybenzylphosphonate. 1H-NMR (CDCl3, 500 MHz) δ 8.42 (d, J=5.2 Hz, 1H), 7.48 (s, 1H), 7.37 (t, J=8.2 Hz, 1H), 7.20 (d, J=5.2 Hz, 1H), 6.98 (m, 1H), 6.86 (s, 1H), 6.71 (s, 1H), 5.18 (d, J=7.3 Hz, 1H), 4.79 (d, J=7.3 Hz, 1H), 3.84 (s, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 160.4, 158.6, 151.1, 150.6, 143.3, 138.0, 130.5, 125.6, 120.3, 118.2, 115.3, 111.6, 85.1, 63.3, 55.5. Mass spec.: 349.0 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f2ba3d0878df4df2a16b236fd3e35a4e
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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