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

HRID 1525154Notes

Reaction equation

HRID 1525154 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.[N:19]1[CH:24]=[C:23](B(O)O)[CH:22]=[N:21][CH:20]=1.COCCOC>O>[F:14][C:13]1([F:15])[CH2:12][O:11][C:10]([NH2:16])=[N:9][C@@:8]21[C:17]1[C:5](=[CH:4][CH:3]=[C:2]([C:23]3[CH:24]=[N:19][CH:20]=[N:21][CH:22]=3)[CH:18]=1)[CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 2795193(Pyrimidin-5-yl)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 71059374(R)-5',5'-Difluoro-6-(pyrimidin-5-yl)-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 pyrimidin-5-ylboronic acid in a 3:1-mixture of 1,2-dimethoxyethane and water as the solvent yielded the title compound (19% yield) as an off-white solid. MS (ISP): m/z=317.0 [M+H]+.

Sources & evidence

ORD record
ord-ddcd8176b4fd460f8654470a429c7b7a
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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