Potassium Carbonate → N-cyclopropyl-4-[8-(isobutylamino)-6-(phenylethynyl)imidazo[1,2-a]pyrazin-3-yl]benzenesulfonamide

HRID 1498607Notes

Reaction equation

HRID 1498607 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH:21]4[CH2:23][CH2:22]4)(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)O1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(O)CC>[CH:21]1([NH:20][S:17]([C:14]2[CH:15]=[CH:16][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([C:37]#[C:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:3]=[C:4]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:5]4=[N:10][CH:9]=3)=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 117363112-Phenyl-1-ethynylboronic acid pinacol esterHCID 866920204-[6-bromo-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylbenzene sulfonamide

Product 1

HCID 54767155N-cyclopropyl-4-[8-(isobutylamino)-6-(phenylethynyl)imidazo[1,2-a]pyrazin-3-yl]benzenesulfonamideYield 14.6%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 30 mg (65 μmol) 4-[6-bromo-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylbenzene sulfonamide which was prepared according to intermediate example 2a, 29.5 mg 4,4,5,5-tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane, 1.0 mL n-propanol, 97 μL of an aqueous 2M potassium carbonate solution, 0.85 mg triphenylphosphine, and 4.55 mg bis(triphenylphosphine)palladium (II) chloride was stirred at 120° C. for 2 hours. The solution was cooled, water added and extracted with dichloromethane. The organic phase was dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 4.6 mg (14%) of the title compound.

Workup

  1. customwas prepared
  2. temperatureThe solution was cooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationAfter filtration and removal of solvent the residue
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-2e3299529d1e4c0b98a4727b8d0eced6
Source dataset
uspto-grants-2015_12
Patent number
US09199999B2

Reaction notes

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