2-Methyl-3-butyn-2-ol → HCID 59436018, compound

HRID 1802500Notes

Reaction equation

HRID 1802500 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1.C(N(CC)CC)C.[CH3:33][C:34]([OH:38])([C:36]#[CH:37])[CH3:35]>CN(C=O)C.[Cu]I.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:37]#[C:36][C:34]([OH:38])([CH3:35])[CH3:33])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1

Participants

7

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 59436068HCID 59436068, compound

Product 1

HCID 59436018HCID 59436018, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-[(2,6-dichloro-4-iodophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one (50 mg, 0.10 mmol) in DMF (4 mL) were added CuI (3.94 mg, 0.02 mmol), triethylamine (30 uL, 0.20 mmol), tetrakis(triphenylphosphine)palladium (0) (12 mg, 10.4 umol), and 2-methylbut-3-yn-2-ol (17.4 mg, 0.21 mmol). The mixture was degassed by bubbling nitrogen gas and heated to 80° C. overnight. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc. The organic layers were combined, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH) afforded the title compound.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen gas
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with water
  5. extractionextracted with EtOAc
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH)

Sources & evidence

ORD record
ord-3aabb94f39e14458aa9ad5bb76b50901
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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