Quinoline-3-boronic acid → HCID 86680683, compound

HRID 1615446Notes

Reaction equation

HRID 1615446 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.[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33](B(O)O)[CH:32]=1>>[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33]([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:32]=1

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680683HCID 86680683, compoundYield 24%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and quinolin-3-ylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a yellow solid (24% yield); 1H-NMR (d6-DMSO) 0.97 (9H, s), 3.78 (2H, t), 4.18 (3H, t), 6.69 (1H, s), 7.55-7.59 (1H, m), 7.66-7.70 (1H, m), 7.92-8.00 (2H, m), 8.08 (1H, d), 8.77 (1H, d); 13C-NMR (CDCl3) 27.7, 41.7, 66.9, 126.8, 127.4, 128.7, 129.2, 133.6, 148.8; MS ES(+) 313.0 (M++1); HRMS m/z calcd for C18H20N2O3+H+ 313.1552 [M+H+]. Found 313.1556. IR λmax=1697, 1636 cm−1.

Sources & evidence

ORD record
ord-9a2313b8ba9a4dbf95442391569f88ed
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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