Potassium Carbonate → [5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yloxy]-acetic acid methyl ester

HRID 33811ノート

反応式

HRID 33811 の反応式
N[C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[C:8]([C:16]4[O:17][C:18]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[CH:19][C:20](=[O:22])[CH:21]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:13]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-:30].[K+].[K+].[CH3:35][O:36][C:37](=[O:40])[CH2:38]Br>CN(C=O)C>[CH3:35][O:36][C:37](=[O:40])[CH2:38][O:30][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][C:8]=3[C:16]3[O:17][C:18]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][C:20](=[O:22])[CH:21]=3)[CH2:13][C:14]=2[CH:15]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 221394022-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

生成物 1

HCID 86596854[5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yloxy]-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one (1.01 g, 2.56 mmol) in anhydrous DMF (25 ml) was added powdered potassium carbonate (716 mg, 5.18 mmol) followed by methylbromoacetate (400 μl, 4.1 mmol). The reaction was stirred at room temperature for 100 hours whereupon it was quenched by dropwise addition of water (75 ml). The mixture was extracted using EtOAc (3×30 ml). The organic extracts were then combined, dried using MgSO4, filtered and concentrated in vacuo to give the title compound as a brown oil that was used without further purification (1.02 g, 85.7%), m/z (LC-MS, ESP), RT=4.05 min, (M++1)=466

後処理

  1. customwas quenched by dropwise addition of water (75 ml)
  2. extractionThe mixture was extracted
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-64febad9b7f94065ae4c87c895d1f4f6
出典データセット
uspto-grants-2008_09
特許番号
US07429660B2

反応ノート

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