5-Chloropyridine-3-boronic acid → HCID 71059748, compound

HRID 1525177Notes

Reaction equation

HRID 1525177 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]3)[CH2:10][C:9]([CH3:21])([CH3:20])[O:8][C:5]2=[CH:6][CH:7]=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:3]=[C:4]3[C@@:11]4([C:16]([F:17])([F:18])[CH2:15][O:14][C:13]([NH2:19])=[N:12]4)[CH2:10][C:9]([CH3:21])([CH3:20])[O:8][C:5]3=[CH:6][CH:7]=2)[CH:26]=[N:27][CH:28]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059649HCID 71059649, compound2×

Product 1

HCID 71059748HCID 71059748, compoundYield 78%

Procedure

In a manner analogous to that described in Example 19, the cross coupling reaction of (R)-6-bromo-5′,5′-difluoro-2,2-dimethyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]oxazin]-2′-amine (intermediate B6.5) with 5-chloropyridin-3-ylboronic acid yielded the title compound (78% yield) as a white powder. MS (ISP): m/z=394.1 [M+H]+.

Sources & evidence

ORD record
ord-89aa7175f0d6471c9613a015b8e2a4e8
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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