5-Chloropyridine-3-boronic acid → HCID 71059504, compound

HRID 1525151Notes

Reaction equation

HRID 1525151 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.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1>>[Cl:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:19]=[C:18]3[C:5]([C:6]([F:20])([F:21])[CH2:7][CH2:8][C@@:9]43[C:14]([F:16])([F:15])[CH2:13][O:12][C:11]([NH2:17])=[N:10]4)=[CH:4][CH:3]=2)[CH:26]=[N:27][CH:28]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059434HCID 71059434, compound

Product 1

HCID 71059504HCID 71059504, compoundYield 28%

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-chloropyridin-3-ylboronic acid yielded the title compound (28% yield) as a white solid. MS (ISP): m/z=399.9 [M+H]+.

Sources & evidence

ORD record
ord-dfe46607b4594e258244442fb257e835
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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