Benzo[b]furan-2-boronic acid → HCID 86680682, compound

HRID 1615445Notes

Reaction equation

HRID 1615445 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.[O:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[CH:33]=[C:32]1B(O)O>>[O:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[CH:33]=[C:32]1[C:18]1[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=1

Participants

3

Reactant 2

HCID 2776266Benzo[b]furan-2-boronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680682HCID 86680682, compoundYield 58%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and benzofuran-2-ylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a yellow solid (58% yield); 1H-NMR (d6-DMSO) 1.08 (9H, s), 3.70 (2H, m), 4.18 (3H, m), 6.68 (1H, s), 6.77 (1H, s), 7.18-7.25 (2H, m), 7.48-7.56 (2H, m); 13C-NMR (CDCl3) 27.7, 41.3, 67.2, 100.7, 110.6, 120.4, 122.8, 123.4, 134.2; MS ES(+) 246.1 (M+-tBu); Anal. Calcd for C17H19NO4: C, 67.76; H, 6.35; N, 4.65. Found: C, 67.34; H, 6.38; N, 4.68. IR λmax=1690 cm−1.

Sources & evidence

ORD record
ord-9858711941cb4dec87153bb2ed8a5627
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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