1,2-Dimethoxyethane → (R)-3-(2'-Amino-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazine]-6-yl)benzonitrile

HRID 1525157Notes

Reaction equation

HRID 1525157 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.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20].COCCOC>O>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:15])([F:14])[C@@:8]2([C:17]3[C:5](=[CH:4][CH:3]=[C:2]([C:25]4[CH:26]=[C:21]([CH:22]=[CH:23][CH:24]=4)[C:19]#[N:20])[CH:18]=3)[CH2:6][CH2:7]2)[N:9]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 27343253-Cyanophenylboronic acidHCID 71059702(R)-6-bromo-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine

Product 1

HCID 71059644(R)-3-(2'-Amino-5',5'-difluoro-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazine]-6-yl)benzonitrileYield 10%

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 3-cyanophenylboronic acid in a 3:1-mixture of 1,2-dimethoxyethane and water as the solvent yielded the title compound (10% yield) as an off-white solid. MS (ISP): m/z=340.2 [M+H]+.

Sources & evidence

ORD record
ord-966273d9befe4fe081030806727e0b90
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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