1,2-Dimethoxyethane → HCID 178419929, compound

HRID 1408412Notes

Reaction equation

HRID 1408412 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.COCCOC.I[C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.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>[O:24]1[C:19]2[CH:18]=[CH:17][C:16]([C:3]3[CH:4]=[CH:5][NH:1][N:2]=3)=[CH:25][C:20]=2[CH2:21][CH2:22][CH2:23]1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 109451636-IodochromanHCID 178514837HCID 178514837, compound

Product 1

HCID 178419929HCID 178419929, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of B-(1H-pyrazol-3-yl)boronic acid (400 mg, 3.57 mmol) in a mixture of tetrahydrofuran (THF), 1,2-dimethoxyethane and water (1:2:1), was added 3,4-dihydro-6-iodo-2H-1-benzopyran (1.53 g, 5.88 mmol; prepared according to Muraki et al., Tetrahedron Lett. 1996, 37, 2441) under nitrogen atmosphere. Then potassium carbonate (980 mg, 7.14 mmol) and bis(triphenylphosphine)palladium(II) dichloride (120 mg, 0.017 mmol) were added, and the reaction mixture was heated at 90° C. for 3 h. The reaction mixture was concentrated and purified by silica gel column chromatography using 30% ethyl acetate in petroleum ether as eluant to provide the title product as solid (100 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3895e9855b84ec2afb67a1d196ad008
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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