2-Methyl-3-butyn-2-ol → HCID 21198474, compound

HRID 1066352Notes

Reaction equation

HRID 1066352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](Cl)=[C:11]1[C:6]([CH:7]=[CH:8][C:9]([O:17][CH3:18])=[CH:10]1)=[N:5]2.[CH3:19][C:20]([OH:24])([C:22]#[CH:23])[CH3:21]>C(N(CC)CC)C.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][C:20]([OH:24])([C:22]#[C:23][C:12]1[C:13]2[C:4]([N:5]=[C:6]3[C:11]=1[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=[CH:7]3)=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=2)[CH3:21]

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 665773,9-Dichloro-7-methoxyacridine

Product 1

HCID 21198474HCID 21198474, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 6,9dichloro-2-methoxyacridine (3.5 g, 12.6 mmol), 2-methyl-3-butyn-2-ol (1.27 g, 15 mmol), dichlorobis(triphenylphosphine)palladium (100 mg), and cuprous iodide (25 mg) in triethylamine (35 mL) and dimethylformamide (20 mL) was heated at 90° for 12 h. The mixture was cooled and diluted with aqueous potassium carbonate to give the title compound. MS(ES) m/e 326.2 (M+H)+.

Workup

  1. temperaturewas heated at 90° for 12 h
  2. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-17484f3f9ff14b0bb34a73a1096e7222
Source dataset
uspto-grants-2001_06
Patent number
US06242459B1

Reaction notes

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