Cesium carbonate → 3-(1-Hydroxyethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one

HRID 634362

反応式

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].CC1(C)C(C)(C)OB([C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:24]1[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:26][CH:25]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

参加物

実験手順

The title compound was made in a similar way as that of the intermediate B1, using 4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.36 g, 1.35 mmol), 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)-morpholine (0.45 g, 1.35 mmol), Pd(PPh3)4 (0.078 g, 0.068 mmol) and Cs2CO3 (0.53 g, 1.6 mmol). The crude was filtered, diluted with 1M HClaqueous (3 ml) and purified via reverse phase chromatography with a Biotage C18 SNAP 120 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%); Phase B ACN 99.9%, formic acid 0.1%) to afford the title compound (0.179 g, 33%).

後処理

filtrationThe crude was filtered
additiondiluted with 1M HClaqueous (3 ml)
custompurified via reverse phase chromatography with a Biotage C18 SNAP 120 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%)

出典と根拠

ORDレコード: ord-afa818dd489e4ba094a373f5f0c4aa08
出典データセット: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09321776B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

関連ノート