5-Chloropyridine-3-boronic acid → (2RS,4R)-6-(5-Chloropyridin-3-yl)-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine

HRID 1525196Notes

Reaction equation

HRID 1525196 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][CH:9]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[Cl:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[N:32][CH:33]=1>>[Cl:27][C:28]1[CH:29]=[C:30]([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][CH:9]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[O:8][C:5]3=[CH:6][CH:7]=2)[CH:31]=[N:32][CH:33]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059735(2RS,4R)-6-bromo-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine

Product 1

HCID 71059566(2RS,4R)-6-(5-Chloropyridin-3-yl)-6',6'-difluoro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amineYield 7%

Procedure

The cross coupling reaction of (2RS,4R)-6-bromo-6′,6′-difluoro-2-phenyl-6′,7′-dihydro-2′H-spiro[chroman-4,5′-[1,4]oxazepin]-3′-amine (intermediate C3.4) with 5-chloropyridin-3-ylboronic acid yielded the title compound (7% yield) as a white solid.

Sources & evidence

ORD record
ord-bd221f27e81244a79d412bb92564caa2
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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