Dimethylformamide → HCID 68676478, compound

HRID 1713709Notes

Reaction equation

HRID 1713709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[C:4](I)[CH:3]=1.CN(C)C=O.[CH2:24]([O:27][CH:28]([CH3:32])[C:29]([OH:31])=[O:30])[C:25]#[CH:26].[CH2:33](NCC)[CH3:34]>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.O>[CH2:33]([O:30][C:29](=[O:31])[CH:28]([O:27][CH2:24][C:25]1[N:8]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:5]2[C:4]([CH:26]=1)=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH3:32])[CH3:34]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 147433122-(prop-2-ynyloxy)propanoic acidHCID 67526223HCID 67526223, compound

Product 1

HCID 68676478HCID 68676478, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 600 mg (1.52 mM) of N-(4-chloro-2-iodophenyl)benzenesulfonamide (Preparation 120) and 0.5 ml of dimethylformamide is prepared in a microwave reaction tube and 14 mg (0.076 mM) of cuprous iodide, 27 mg (0.038 mM) of bis(triphenylphosphine)dichloropalladium, 357 mg (2.3 mM) of the ethyl ester of 2-(2-propynyloxy)propanoic acid and, finally, 0.5 ml of diethylamine are added. The mixture is heated by microwaves at 130° C. for 15 min and then cooled and hydrolyzed with 10 ml of water. The mixture is extracted three times with 15 ml of ethyl acetate and the combined organic phases are washed with water and then dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (95/5; v/v) as the eluent to give 0.44 g of the expected compound in the form of a yellow oil (yield=69%).

Workup

  1. temperaturecooled
  2. extractionThe mixture is extracted three times with 15 ml of ethyl acetate
  3. washthe combined organic phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-cb6057b1eeea46cdae30b3e85c3c3a82
Source dataset
uspto-grants-2010_09
Patent number
US07795297B2

Reaction notes

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