Nitrogen → methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate

HRID 1894772ノート

反応式

HRID 1894772 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].N#N>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.O.COCCOC>[CH2:13]([CH:12]([CH2:15][CH3:16])[CH:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=3)[S:3][C:4]=2[CH:10]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[CH3:14]

参加物

8

反応物 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 54759530HCID 54759530、化合物

生成物 1

HCID 54761530methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-bromo-6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole (93 mg, 0.255 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (50.6 mg, 0.281 mmol), tetrakis(triphenylphosphine)palladium (29.5 mg, 0.0255 mmol), potassium carbonate (106 mg, 0.765 mmol), DME (5 mL) and water (0.8 mL) was degassed, filled with N2, and heated to 80° C. for 6 h. The reaction mixture was evaporated. The crude product was purified by column chromatography using 5% MeOH in DCM as eluent to afford to methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate as white solid. MS (ES+): m/z 420.28 (MH+).

後処理

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-66d1b5318c8442098698fe83310e962e
出典データセット
uspto-grants-2013_08
特許番号
US08513291B2

反応ノート

読み込み中…