2-Fluoropyridine-4-boronic acid → HCID 57671648, compound

HRID 553523Notes

Reaction equation

HRID 553523 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16].[F:26][C:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29][N:28]=1>>[F:26][C:27]1[CH:32]=[C:31]([C:9]2[CH:10]=[C:11]3[C:6](=[N:7][CH:8]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])=[C:2]3[OH:1])[CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 57671542HCID 57671542, compound

Product 1

HCID 57671648HCID 57671648, compound

Procedure

The title compound was prepared similarly to the procedures described for Example 64 (a, b) from tert-butyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetate (Example 26 (g)) and 2-fluoro-4-pyridinylboronic acid. MS (ESI, pos. ion) m/z: 373 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm: 12.99 (s, 1 H), 10.34-10.48 (m, 1 H), 9.31 (s, 1 H), 8.80 (s, 1 H), 8.30-8.41 (m, 1 H), 7.84-7.96 (m, 1 H), 7.78 (s, 1 H), 4.04-4.25 (m, 2 H), 3.72 (s, 3 H).

Sources & evidence

ORD record
ord-8e89b05a0c5b44fea451c97095509b93
Source dataset
uspto-grants-2011_11
Patent number
US08048892B2

Reaction notes

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