Potassium Phosphate, Tribasic → [4-(6-Hydroxy-benzothiazol-2-yl)-phenyl]-(4-methyl-piperidin-1-yl)-methanone

HRID 579453ノート

反応式

HRID 579453 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=2)=[O:20])[CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCCO)C.O.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:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:24]3[CH:23]=[CH:22][C:21]([C:19]([N:16]4[CH2:15][CH2:14][CH:13]([CH3:12])[CH2:18][CH2:17]4)=[O:20])=[CH:26][CH:25]=3)[S:3][C:4]=2[CH:10]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 441185274-(4-Methylpiperidine-1-carbonyl)phenylboronic acidHCID 451167822-Bromo-1,3-benzothiazol-6-ol

生成物 1

HCID 67448530[4-(6-Hydroxy-benzothiazol-2-yl)-phenyl]-(4-methyl-piperidin-1-yl)-methanone収率 20.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8076Glycol monoethyl ether溶媒

反応条件

温度
115 °C

実験手順

2-Bromo-6-hydroxybenzothiazole (400 mg, 1.74 mmol), 4-(4-methylpiperidine-1-carbonyl)phenylboronic acid (472 mg, 1.91 mmol), potassium phosphate (848 mg, 6.96 mmol) and tetrakis(triphenylphosphine)palladium (60 mg, 0.05 mmol) were dissolved in a mixture of 1.3.5 mL 2-ethoxyethanol and 1.5 mL water. The mixture was stirred at 115° C. under argon for 2 h. The reaction mixture was let to reach room temperature then activated-carbon was added and stirred for 20 min. The mixture was filtered, the solid was washed with ethanol and the combined filtrates were evaporated. The residue was purified by column chromatography (Kieselgel 60) with chloroform as the eluent. The crude product was triturated with Et2O, collected and air dried, affording the title compound (122 mg, 0.35 mmol, 20%).

後処理

  1. customto reach room temperature
  2. additionwas added
  3. stirringstirred for 20 min
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with ethanol
  6. customthe combined filtrates were evaporated
  7. customThe residue was purified by column chromatography (Kieselgel 60) with chloroform as the eluent
  8. customThe crude product was triturated with Et2O
  9. customcollected
  10. customair dried

出典と根拠

ORDレコード
ord-af54cfcf66914d4981bdf54fb239216d
出典データセット
uspto-grants-2015_05
特許番号
US09040714B2

反応ノート

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