5-Chloropyridine-3-boronic acid → HCID 71059426, compound

HRID 1525181Notes

Reaction equation

HRID 1525181 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C@@:5]12[C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][CH:26]=1>>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[S:8][CH2:7][CH2:6][C@@:5]23[C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]2)[CH:24]=[N:25][CH:26]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059612HCID 71059612, compound2×

Product 1

HCID 71059426HCID 71059426, compoundYield 70%

Procedure

In a manner analogous to that described in Example 19, the cross coupling reaction of (R)-6′-bromo-5,5-difluoro-5,6-dihydrospiro[[1,3]oxazine-4,4′-thiochroman]-2-amine (intermediate B6.9) with 5-chloropyridin-3-ylboronic acid yielded the title compound (70% yield) as a white solid. MS (ISP): m/z=382.0 [M+H]+.

Sources & evidence

ORD record
ord-c5afb6bade044d3f92aec55aaf3a1996
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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