3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 59596302, compound

HRID 2264733Notes

Reaction equation

HRID 2264733 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)=[CH:3][C:2]=1[C:30]1[CH:29]=[N:28][CH:27]=[C:26]([F:25])[CH:31]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59596252HCID 59596252, compound

Product 1

HCID 59596302HCID 59596302, compoundYield 31%

Procedure

The title compound was synthesized from 1-(3-bromo-4-fluorophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine (Scheme #11, G) as described in Example 67 (Scheme #10, D) in 31% yield using 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. 1H NMR (DMSO-d6) δ 8.63 (d, J=2.78 Hz, 1 H), 8.57-8.51 (m, 1 H), 8.50-8.42 (m, 2 H), 7.95-7.86 (m, 2 H), 7.85-7.78 (m, 1 H), 7.56-7.46 (m, 4 H), 7.36-7.27 (m, 3 H), 6.96 (br s, 2 H), 1.91 (s, 2.5 H); MS (ESI) m/z 399 [M+1]+.

Sources & evidence

ORD record
ord-8f1ddf881b1f47c78826470f29bc92ff
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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