1,2-Dimethoxyethane → (R)-6-(5-Chloropyridin-3-yl)-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine

HRID 1525156Notes

Reaction equation

HRID 1525156 reaction equation
Br[C:2]1[CH:18]=[C:17]2[C:5]([CH2:6][CH2:7][C@@:8]32[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]3)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[N:24][CH:25]=1.COCCOC>O>[Cl:19][C:20]1[CH:21]=[C:22]([C:2]2[CH:18]=[C:17]3[C:5]([CH2:6][CH2:7][C@@:8]43[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]4)=[CH:4][CH:3]=2)[CH:23]=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 201118775-Chloropyridine-3-boronic acidHCID 71059702(R)-6-bromo-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine

Product 1

HCID 71059337(R)-6-(5-Chloropyridin-3-yl)-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amineYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner analogous to that described in Example 1, the cross-coupling reaction of (R)-6-bromo-5′,5′-difluoro-2,3,5′,6′-tetrahydrospiro[indene-1,4′-[1,3]oxazin]-2′-amine (intermediate A6.5) with 5-chloropyridin-3-ylboronic acid in a 3:1-mixture of 1,2-dimethoxyethane and water as the solvent yielded the title compound (19% yield) as a white solid. MS (ISP): m/z=349.8 [M+H]+.

Sources & evidence

ORD record
ord-d38b8c7bcb6c40688260ae8af587141b
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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