3-Cyanophenylboronic acid → tert-butyl 5-(3-cyanophenyl)-2H-1,4-oxazine-4(3H)-carboxylate

HRID 1615428Notes

Reaction equation

HRID 1615428 reaction equation
O(P(O[C:18]1[N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32]>>[C:31]([C:33]1[CH:38]=[C:37]([C:18]2[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=2)[CH:36]=[CH:35][CH:34]=1)#[N:32]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680665tert-butyl 5-(3-cyanophenyl)-2H-1,4-oxazine-4(3H)-carboxylateYield 63%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 3-cyanophenylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as an off-white solid (63% yield); 1H-NMR (d6-DMSO) 1.08 (9H, s), 3.69 (2H, t), 4.12 (2H, t), 6.61 (1H, s), 7.50-7.52 (2H, m), 7.62-7.66 (2H, m); MS ES(+) 231.0 (M+-tBu). IR λmax=2225, 1697 cm−1

Sources & evidence

ORD record
ord-4b49c24cc79542b08b13d7f7fb70596c
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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