4-Cyanophenylboronic acid → HCID 86680664, compound

HRID 1615427Notes

Reaction equation

HRID 1615427 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:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)#[N:32]>>[C:31]([C:33]1[CH:38]=[CH:37][C:36]([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:35][CH:34]=1)#[N:32]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680664HCID 86680664, compoundYield 58%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 4-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 (58% yield); 1H-NMR (d6-DMSO) 1.09 (9H, s), 3.68 (2H, t), 4.13 (2H, t), 6.68 (1H, s), 7.37 (2H, d), 7.74 (2H, d); 13C-NMR (CDCl3) 27.7, 41.5, 66.8, 125.1, 131.8, 134.4; MS ES(+) 287.0 (M++1). IR λmax=2227, 1699 cm−1.

Sources & evidence

ORD record
ord-bf3f678f21314eac90435a1b91581c18
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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