Morpholine → (E)-N-(2,4-dimethylphenyl)-N-isobutyl-4-(3-morpholinoprop-1-en-1-yl)benzenesulfonamide

HRID 1487081Notes

Reaction equation

HRID 1487081 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:25]/[CH:26]=[CH:27]/[B-](F)(F)F.[K+].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.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>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:27]=[CH:26]/[CH2:25][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 23693094Potassium trans-3-bromo-1-propenyltrifluoroborateHCID 867315904-bromo-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide

Product 1

HCID 89875709(E)-N-(2,4-dimethylphenyl)-N-isobutyl-4-(3-morpholinoprop-1-en-1-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 4-bromo-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (200 mg, 0.505 mmol), potassium trans-3-bromo-1-propenyltrifluoroborate (126 mg, 0.555 mmol), morpholine (0.088 mL, 1.009 mmol), bis(triphenylphosphine)palladium(II) chloride (10.63 mg, 0.015 mmol) and cesium carbonate (493 mg, 1.514 mmol) was prepared in dimethyl sulfoxide (DMSO) (1 mL). The reaction was then heated by microwaves, to 140° C. for 30 minutes. The reaction was then passed through a sulfonic acid (SCX) solid phase extraction (SPE) cartridge, eluting with methanol followed by ammonia in methanol, then concentrated under a stream of nitrogen. Purification was carried out by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated and combined to give the desired product, 23.2 mg. LCMS [LCMS2] Rt 1.41 min, m/z (ES+) 443 (M+H).

Workup

  1. extractionThe reaction was then passed through a sulfonic acid (SCX) solid phase extraction (SPE) cartridge
  2. washeluting with methanol
  3. concentrationconcentrated under a stream of nitrogen
  4. customPurification
  5. concentrationThe relevant fractions were concentrated

Sources & evidence

ORD record
ord-00a1775eecdb46b6a9f67dd7d2a1525c
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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