Tolylboronic acid → HCID 24871615, compound

HRID 2106311Notes

Reaction equation

HRID 2106311 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.B(O)(O)[C:33]1[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=1>COCCOC>[C:18]1([N:13]2[C:12]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 79799Tolylboronic acidHCID 86598385HCID 86598385, compound

Product 1

HCID 24871615HCID 24871615, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (17.5 mg) was prepared from 188.9 mg of 2-phenyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 176, Step B) and 93.3 mg of p-tolylboronic acid as in Example 199, using DME as the solvent. MS (ESI): exact mass calculated for C20H21N3, 303.17; found, m/z 304.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.26-7.23 (m, 2H), 7.21-7.16 (m, 3H), 7.15-7.12 (m, 2H), 7.04-7.01 (m, 2H), 3.11-3.07 (m, 2H), 3.04-3.00 (m, 2H), 2.98-2.96 (m, 2H), 2.68-2.65 (m, 2H), 2.35 (s, 3H).

Sources & evidence

ORD record
ord-5cc7127eba8640f8905a7703a7b19a26
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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