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 1525154ノート

反応式

HRID 1525154 の反応式
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

参加物

5

反応物 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

生成物 1

HCID 71059374(R)-5',5'-Difluoro-6-(pyrimidin-5-yl)-2,3,5',6'-tetrahydrospiro[indene-1,4'-[1,3]oxazin]-2'-amine収率 19%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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]+.

出典と根拠

ORDレコード
ord-ddcd8176b4fd460f8654470a429c7b7a
出典データセット
uspto-grants-2015_07
特許番号
US09079919B2

反応ノート

読み込み中…