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

HRID 579453Notes

Reaction equation

HRID 579453 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
115 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-af54cfcf66914d4981bdf54fb239216d
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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