1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 86680681, compound

HRID 1615444Notes

Reaction equation

HRID 1615444 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.[CH3:31][N:32]1[C:40]2[C:35](=[C:36](B3OC(C)(C)C(C)(C)O3)[CH:37]=[CH:38][CH:39]=2)[CH:34]=[N:33]1>>[CH3:31][N:32]1[C:40]2[C:35](=[C:36]([C:18]3[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=3)[CH:37]=[CH:38][CH:39]=2)[CH:34]=[N:33]1

Participants

3

Reactant 2

HCID 454801871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680681HCID 86680681, compoundYield 45%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a brown solid (45% yield); 1H-NMR (d6-DMSO) 0.80 (9H, s), 3.81 (2H, m), 4.02 (3H, s), 4.18 (2H, m), 6.50 (1H, s), 6.94 (1H, d), 7.31 (1H, t), 7.47 (1H, m), 7.90 (1H, s); 13C-NMR (CDCl3) 27.4, 35.4, 41.3, 66.8, 107.0, 116.5, 126.2, 131.8; MS ES(+) 316.0 (M++1); HRMS m/z calcd for C17H21N3O3+H+ 316.1661 [M+H+]. Found 316.1664. IR λmax=1692, 1638 cm−1.

Sources & evidence

ORD record
ord-aeea8899a2964a5980f665b31b606760
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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