(5-Fluoropyridin-3-yl)boronic acid → HCID 71059502, compound

HRID 1525152Notes

Reaction equation

HRID 1525152 reaction equation
Br[C:2]1[CH:19]=[C:18]2[C:5]([C:6]([F:21])([F:20])[CH2:7][CH2:8][C@@:9]32[C:14]([F:16])([F:15])[CH2:13][O:12][C:11]([NH2:17])=[N:10]3)=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1>>[F:20][C:6]1([F:21])[C:5]2[C:18](=[CH:19][C:2]([C:25]3[CH:26]=[N:27][CH:28]=[C:23]([F:22])[CH:24]=3)=[CH:3][CH:4]=2)[C@@:9]2([C:14]([F:16])([F:15])[CH2:13][O:12][C:11]([NH2:17])=[N:10]2)[CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 71059434HCID 71059434, compound

Product 1

HCID 71059502HCID 71059502, compoundYield 32%

Procedure

In a manner analogous to that described in Example 1, the cross-coupling reaction of (R)-7-bromo-4,4,5′,5′-tetrafluoro-3,4,5′,6′-tetrahydro-2H-spiro[naphthalene-1,4′-[1,3]oxazin]-2′-amine (intermediate A6.4) with 5-fluoropyridin-3-ylboronic acid yielded the title compound (32% yield) as a pale yellow solid. MS (ISP): m/z=384.0 [M+H]+.

Sources & evidence

ORD record
ord-06537a758311485fa6d635e8cbb7bb00
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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