3,4-Difluorobenzeneboronic acid → HCID 11162904, compound

HRID 2106340Notes

Reaction equation

HRID 2106340 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.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38]>>[CH:18]1([N:13]2[C:12]([C:35]3[CH:34]=[CH:33][C:32]([F:31])=[C:37]([F:38])[CH:36]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 86598377HCID 86598377, compound

Product 1

HCID 11162904HCID 11162904, compoundYield 47.9%

Procedure

The title compound (70 mg) was prepared according to Example 180 using 209 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 218 mg of 3,4-difluorophenylboronic acid. MS (ESI): exact mass calculated for C18H21F2N3, 317.17; found, m/z 318.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.50-7.45 (m, 1H), 7.36-7.32 (m, 1H), 7.18-7.17 (m, 1H), 4.49 (m, 1H), 3.43-3.41 (m, 2H), 3.21-3.19 (m, 2H), 2.80-2.78 (m, 2H), 2.15-1.87 (m, 6H), 1.66-1.61 (m, 2H).

Sources & evidence

ORD record
ord-82c90faad73c4f309d3f1b4ecfbc5c90
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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