1,4-Dioxane → HCID 16742580, compound

HRID 1624982Notes

Reaction equation

[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3I)[C:8]2=[O:18])=[CH:4][CH:3]=1.[NH2:21][CH2:22][C:23]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.N12CCCN=C1CCCCC2.[O:42]1CCOC[CH2:43]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:30][C:23]1([CH2:22][NH:21][C:43]([C:13]2[C:14]3[CH:15]=[CH:16][N:7]([CH2:6][C:5]4[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=4)[C:8](=[O:18])[C:9]=3[CH:10]=[CH:11][CH:12]=2)=[O:42])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 110 °C

Procedure

A 5-mL process vial was charged with 2-(4-fluoro-benzyl)-5-iodo-2H-isoquinolin-1-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) gave 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-c2154160712a4fafb03d8e806f45f563
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

Loading…