2-Fluoropyridine-3-boronic acid → HCID 24874779, compound

HRID 2264758Notes

Reaction equation

HRID 2264758 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][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:26][C:27]1[C:32](B(O)O)=[CH:31][CH:30]=[CH:29][N:28]=1>>[CH2:24]([C:20]1[CH:19]=[C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:32]4[C:27]([F:26])=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:3]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:23]=[CH:22][N:21]=1)[CH3:25]

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596298HCID 59596298, compound

Product 1

HCID 24874779HCID 24874779, compoundYield 61%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-ethylpyridin-4-yl)-1H-isoindol-3-amine (Example 110) as described in Example 67 Scheme #10, D in 61% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.28 (d, J=5.31 Hz, 1 H), 8.20-8.11 (m, 1 H), 7.98-7.89 (m, 1 H), 7.79-7.71 (m, 2 H), 7.47-7.28 (m, 7 H), 7.15-7.10 (m, 1 H), 7.06 (dd, J=5.18, 1.64 Hz, 1 H), 6.83 (br s, 2 H), 2.60 (q, J=7.58 Hz, 2 H), 1.08 (t, J=7.58 Hz, 3 H); MS (ESI) m/z 409 [M+1]+.

Sources & evidence

ORD record
ord-56f598468c89437b849a70c7de8e5ead
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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