Water → HCID 18466520, compound

HRID 2229123Notes

Reaction equation

HRID 2229123 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)=[CH:4][C:3]=1[OH:20].[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:23]([O:20][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)[C:6]([F:8])=[CH:7][C:2]=1[Cl:1])[C:22]#[CH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 18466525HCID 18466525, compound

Product 1

HCID 18466520HCID 18466520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

A mixture of 0.25 g (0.808 mmol) of the compound of Example 7, 0.12 g (0.97 mmol) of propargyl bromide and 0.22 g (1.62 mmol) of potassium carbonate powder in 10 ml of DMF was stirred for 2 h at 65-70° C. After cooling, 50 ml of water were added and the mixture was extracted 3 times with methyl tert-butyl ether, and the extracts were dried and concentrated, affording 0.28 g (100% of theory) of the title compound of mp. 68-70° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted 3 times with methyl tert-butyl ether
  3. customthe extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e29990ca2f6849218da7f36512e41eff
Source dataset
uspto-grants-2002_07
Patent number
US06420314B1

Reaction notes

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