1,4-Dioxane → HCID 24804061, compound

HRID 1624986Notes

Reaction equation

[OH:1][CH2:2][CH:3]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2I)[C:8]1=[O:18])[CH:4]([CH3:6])[CH3:5].[NH2:19][CH2:20][C:21]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N12CCCN=C1CCCCC2.[O:40]1CCOC[CH2:41]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:1][CH2:2][CH:3]([N:7]1[CH:16]=[CH:15][C:14]2[C:13]([C:41]([NH:19][CH2:20][C:21]3([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:40])=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]1=[O:18])[CH:4]([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 110 °C

Procedure

A 5-mL process vial was charged with 2-(1-hydroxy-3-methylbutan-2-yl)-5-iodoisoquinolin-1(2H)-one (100 mg, 0.0004 mol), 1-(aminomethyl)cycloheptanol (200 mg, 0.001 mol), molybdenum hexacarbonyl (90 mg, 0.0004 mol), palladium acetate (8 mg, 0.00004 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (200 mg, 0.001 mol) and 1,4-dioxane (2 mL, 0.02 mol). The vessel was sealed under air and exposed to microwave heating for 15 min at 110° C. The reaction tube was thereafter cooled to room temperature, and the mixture was concentrated and dissolved in a small volume of dichloromethane. The crude product was purified via flash column chromatography (12 g of silica gel, 50-100% etOAC/Hexane) to give the desired product as a white solid.

Workup

customThe vessel was sealed under air
temperatureThe reaction tube was thereafter cooled to room temperature
concentrationthe mixture was concentrated
dissolutiondissolved in a small volume of dichloromethane
customThe crude product was purified via flash column chromatography (12 g of silica gel, 50-100% etOAC/Hexane)

Sources & evidence

ORD record: ord-0514872aaa98410884684611c56afcfa
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

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