1,2-Dimethoxyethane → HCID 86273822, compound

HRID 1497741Notes

Reaction equation

HRID 1497741 reaction equation
[CH3:1][N:2]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)[NH:4][C:3]1=[O:27].I[C:29]1[C:30]([O:35][CH3:36])=[N:31][O:32][C:33]=1[CH3:34].C(=O)([O-])[O-].[K+].[K+].C(COC)OC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:36][O:35][C:30]1[C:29]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3](=[O:27])[N:2]([CH3:1])[CH:11]3[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:33]([CH3:34])[O:32][N:31]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 117600656HCID 117600656, compoundHCID 123205558HCID 123205558, compound

Product 1

HCID 86273822HCID 86273822, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

3-Methyl-4-phenyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinazolin-2-one (457 mg, 1.255 mmol), 4-Iodo-3-methoxy-5-methyl-isoxazole (150 mg, 0.628 mmol), potassium carbonate (173 mg, 1.255 mmol) and Pd(dppf)Cl2 (102.5 mg, 0.126 mmol) are added to a microwave vessel. Dimethoxyethane (0.1 mL) and water (0.1 mL) are added and the vessel flushed with argon. The mixture is heated in a microwave reactor at 120° C. for 3.5 hours. The reaction mixture is extracted with ethyl acetate from water. The organic phase is dried over Na2SO4 and the solvent is removed on a rotary evaporator. The residue is purified by reversed phase HPLC.

Workup

  1. customthe vessel flushed with argon
  2. extractionThe reaction mixture is extracted with ethyl acetate from water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customthe solvent is removed on a rotary evaporator
  5. customThe residue is purified by reversed phase HPLC

Sources & evidence

ORD record
ord-deb3e23ded1d484290e8d4b34fc01b9e
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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