4-Chlorophenylboronic acid → HCID 11392907, compound

HRID 749811Notes

Reaction equation

HRID 749811 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]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:12]2[N:13]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[N:14]=[C:15]3[C:11]=2[CH2:10][CH2:9][NH:8][CH2:17][CH2:16]3)=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 86598377HCID 86598377, compound

Product 1

HCID 11392907HCID 11392907, compoundYield 49.4%

Procedure

The title compound (74 mg) was prepared as in Example 177, Steps C and D, using 215 mg of 2-cyclopentyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 180, Step A) and 296 mg of 4-chlorophenylboronic acid. MS (ESI): exact mass calculated for C18H22ClN3, 315.15; found, m/z 316.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.59-7.53 (m, 2H), 7.36-7.30 (m, 2H), 4.48 (m, 1H), 3.44-3.37 (m, 2H), 3.34-3.27 (m, 2H), 3.22-3.15 (m, 2H), 2.81-2.74 (m, 2H), 2.06-1.84 (m, 6H), 1.65-155 (m, 2H).

Sources & evidence

ORD record
ord-50265d23dfec4c988babc0afabaabe80
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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