2-Fluoropyridine-3-boronic acid → HCID 24874781, compound

HRID 2264760Notes

Reaction equation

HRID 2264760 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:27][C:28]1[C:33](B(O)O)=[CH:32][CH:31]=[CH:30][N:29]=1>>[F:27][C:28]1[C:33]([C:2]2[CH:3]=[C:4]([C:8]3([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[CH:19]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]([NH2:17])=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596314HCID 59596314, compound

Product 1

HCID 24874781HCID 24874781, compoundYield 42%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-isopropylpyridin-4-yl)-1H-isoindol-3-amine (Example 113) as described in Example 67 Scheme #10, D in 42% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.29 (d, J=5.30 Hz, 1 H), 8.19-8.11 (m, 1 H), 7.97-7.90 (m, 1 H), 7.82-7.70 (m, 2 H), 7.49-7.27 (m, 7 H), 7.18-7.11 (m, 1 H), 7.05 (dd, J=5.31, 1.77 Hz, 1 H), 6.84 (br s, 2 H), 2.93-2.77 (m, 1 H), 1.08 (d, J=6.82 Hz, 6 H); MS (ESI) m/z 423 [M+1]+.

Sources & evidence

ORD record
ord-e1b70bc1d71f4694af4ab060c1c4e1db
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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