1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86680680, compound

HRID 1615443Notes

Reaction equation

HRID 1615443 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.[CH2:31]([N:38]1[CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([N:38]1[CH:42]=[C:41]([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:40]=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680680HCID 86680680, compoundYield 43%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a brown solid (43% yield); 1H-NMR (d6-DMSO) 1.12 (9H, s), 3.61 (2H, t), 4.02 (2H, t), 5.24 (2H, s), 6.31 (1H, s), 7.27-7.33 (6H, m), 7.64 (1H, s); 13C-NMR (CDCl3) 27.8, 41.9, 56.2, 66.5, 125.5, 128.1, 128.2, 128.8, 130.9, 136.9; MS ES(+) 342.0 (M++1); HRMS m/z calcd for C19H23N3O3+H+ 342.1818 [M+H+]. Found 342.1826. IR λmax=1697 cm−1.

Sources & evidence

ORD record
ord-5c360796b9644e83bb73d521acaa145b
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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