3,4-Difluorobenzeneboronic acid → HCID 24871620, compound

HRID 2106330Notes

Reaction equation

HRID 2106330 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[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[F:39]>>[CH:18]1([N:13]2[C:12]([C:36]3[CH:35]=[CH:34][C:33]([F:32])=[C:38]([F:39])[CH:37]=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][CH2:23]1

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 86598376HCID 86598376, compound

Product 1

HCID 24871620HCID 24871620, compoundYield 29.4%

Procedure

The title compound (42.7 mg) was prepared as in Example 177, Steps C and D, using 205.2 mg of 2-cyclohexyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 177, Step B) and 224.9 mg of 3,4-difluorophenylboronic acid. MS (ESI): exact mass calculated for C19H23F2N3, 331.40; found, m/z 332.5 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.51-7.44 (m, 1H), 7.34-7.28 (m, 1H), 7.17-7.13 (m, 1H), 3.91-3.84 (m, 1H), 3.42-3.38 (m, 2H), 3.18-3.14 (m, 2H), 2.78-2.74 (m, 2H), 1.96-1.78 (m, 6H), 1.70-1.64 (m, 1H), 1.32-1.19 (m, 3H).

Sources & evidence

ORD record
ord-97c46f4ba8f34c6e852172b6ad82e2d0
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

Loading…