Diisopropylamine → HCID 57751039, compound

HRID 2283316Notes

Reaction equation

HRID 2283316 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH3:13][C:14]([OH:18])([C:16]#[CH:17])[CH3:15].C(NC(C)C)(C)C>CN(C)C=O.[Cu]I.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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:17]#[C:16][C:14]([OH:18])([CH3:15])[CH3:13])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 8207002-Amino-5-bromobenzenesulfonamide

Product 1

HCID 57751039HCID 57751039, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-5-bromobenzenesulfonamide (2 g, 7.96 mmol), copper(I) iodide (0.076 g, 0.40 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.280 g, 0.40 mmol) were slurried in anhydrous N,N-dimethylformamide (6 mL) in a microwave vial. 2-Methyl-3-butyn-2-ol (2.316 mL, 23.89 mmol) followed by diisopropylamine (3.37 mL, 23.89 mmol) were added, the vial was capped, purged with argon and the mixture was heated in a microwave at 100° C. for 30 min. The mixture was filtered and the solvent was evaporated in vacuo. Purification by column chromatography, using a gradient of 60-70% ethyl acetate in heptane as the eluent, gave 0.92 g (46% yield) of the title compound.

Workup

  1. additionwere added
  2. customthe vial was capped
  3. custompurged with argon
  4. filtrationThe mixture was filtered
  5. customthe solvent was evaporated in vacuo
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-1ace700d37784a2ca8010e448c47cdf4
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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