3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 1-(3-Fluoropyridin-4-yl)-1-[3-(5-fluoropyridin-3-yl)phenyl]-1H-isoindol-3-amine

HRID 2264735Notes

Reaction equation

HRID 2264735 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][C:19]=3[F:24])[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:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[F:24][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C:8]1([C:16]2[CH:11]=[CH:12][CH:13]=[C:14]([C:30]3[CH:29]=[N:28][CH:27]=[C:26]([F:25])[CH:31]=3)[CH:15]=2)[C:4]2[C:5](=[CH:6][CH:7]=[CH:2][CH:3]=2)[C:10]([NH2:17])=[N:9]1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 595962811-(3-Bromophenyl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 595962631-(3-Fluoropyridin-4-yl)-1-[3-(5-fluoropyridin-3-yl)phenyl]-1H-isoindol-3-amineYield 57%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine (Scheme #12, I) as described in Scheme #10, D in 57% yield using 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. 1H NMR (DMSO-d6) δ 8.58-8.52 (m, 1 H), 8.49 (d, J=2.78 Hz, 1 H), 8.37 (d, J=2.78 Hz, 1 H), 8.27 (d, J=4.80 Hz, 1 H), 7.88-7.82 (m, 1 H), 7.81-7.72 (m, 2 H), 7.60-7.53 (m, 1 H), 7.51-7.40 (m, 3 H), 7.35 (t, J=7.71 Hz, 1 H), 7.30-7.25 (m, 1 H), 7.21 (dd, J=6.82, 5.05 Hz, 1 H), 6.95 (br s, 2 H), 1.84 (s, 1.4 H); MS (ESI) m/z 399 [M+1]+.

Sources & evidence

ORD record
ord-a0131b31d2634f38bfedc4467fd5dfeb
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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