4-Fluorophenylboronic acid → HCID 11243918, compound

HRID 2106392Notes

Reaction equation

[O-]S([C:5](F)(F)F)(=O)=O.FC1C=CC(B(O)O)=CC=1.[CH:19]1([N:24]2[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[C:32]3[C:26]([CH2:27][CH2:28][NH:29][CH:30](C)[CH2:31]3)=[N:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([N:24]2[C:33]([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)=[C:32]3[C:26]([CH2:27][CH:28]([CH3:5])[NH:29][CH2:30][CH2:31]3)=[N:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Reactant 3

HCID 2856454-Fluorophenylboronic acid

HCID 2758875Trifluoromethanesulfonate

HCID 11472471HCID 11472471, compound

Product 1

HCID 11243918HCID 11243918, compound

Procedure

The title compound (160.4 mg) was prepared as in Example 263 from 301 mg of the triflate from Step B and 185 mg of 4-fluorophenylboronic acid. The sequence also produced 2-cyclopentyl-3-(4-fluoro-phenyl)-5-methyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene. The isomers were separated by SFC chromatography. MS (ESI): exact mass calculated for C19H24FN3, 313.41; found, m/z 314.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.25-7.21 (m, 2H), 7.18-7.12 (m, 2H), 4.22 (m, 1H), 3.24-3.18 (m, 1H), 3.03-2.92 (m, 2H), 2.76-2.67 (m, 2H), 2.60-2.52 (m, 1H), 2.45-2.39 (m, 1H), 2.16-1.82 (m 6H), 1.59-1.47 (m, 2H), 1.25 (d, J=6.3 Hz, 3H).

Workup

customThe isomers were separated by SFC chromatography

Sources & evidence

ORD record: ord-f16bfdc572b74970a4e85ec310d35dc8
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579470B2

Reaction notes

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