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

HRID 579453노트

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HRID 579453 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8076Glycol monoethyl ether용매

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온도
115 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-af54cfcf66914d4981bdf54fb239216d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040714B2

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