5-Chloropyridine-3-boronic acid → HCID 71059652, compound

HRID 1525194Notes

Reaction equation

HRID 1525194 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:17]([F:19])([F:18])[CH2:16][O:15][CH2:14][C:13]([NH2:20])=[N:12]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[N:26][CH:27]=1>>[Cl:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[C:4]3[C@@:11]4([C:17]([F:19])([F:18])[CH2:16][O:15][CH2:14][C:13]([NH2:20])=[N:12]4)[CH2:10][CH2:9][O:8][C:5]3=[CH:6][CH:7]=2)[CH:25]=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059576HCID 71059576, compound

Product 1

HCID 71059652HCID 71059652, compoundYield 35%

Procedure

The cross coupling reaction of (R)-6-bromo-6′,6′-difluoro-6′,7′-dihydro-2′H-spiro[chroman-4,5′-[1,4]oxazepin]-3′-amine (intermediate C3.2) with 5-chloropyridin-3-ylboronic acid yielded the title compound (35% yield) as a light brown, amorphous material. MS (ISP): m/z=380.2 [M+H]+.

Sources & evidence

ORD record
ord-c79b40c297e84a52be30ecfa42aba585
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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