4-Fluorophenylboronic acid → HCID 59752594, compound

HRID 749845Notes

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][C:20]([CH3:24])([CH3:23])[CH2:19]3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>>[CH3:24][C:20]1([CH3:23])[CH2:21][CH2:22][CH:18]([N:13]2[C:12]([C:37]3[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH2:19]1

Participants

Reactant 2

HCID 2856454-Fluorophenylboronic acid

HCID 86598389HCID 86598389, compound

Product 1

HCID 59752594HCID 59752594, compoundYield 38.4%

Procedure

The title compound (52.6 mg) was prepared as in Example 177, Steps C and D, using 201.7 mg of 2-(3,3-dimethyl-cyclopentyl)-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 221, Step A) and 180 mg of 4-fluorophenylboronic acid. MS (ESI): exact mass calculated for C20H26FN3, 327.44; found, m/z 328.5 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.39-7.34 (m, 2H), 7.33-7.28 (m, 2H), 4.62-4.53 (m, 1H), 3.44-3.39 (m, 2H), 3.31-3.29 (m, 2H), 3.21-3.17 (m, 2H), 2.80-2.75 (m, 2H), 2.20-2.03 (m, 2H), 2.00-1.94 (m, 1H), 1.80-1.73 (m, 2H), 1.49-1.41 (m, 1H), 1.16 (s, 3H), 0.93 (s, 3H).

Sources & evidence

ORD record: ord-d85bbf4186f8481f8e41564e0c52a837
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402680B2

Reaction notes

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