1,4-Dioxane → HCID 68347608, compound

HRID 1624999Notes

Reaction equation

HRID 1624999 reaction equation
[C:1]([O:4][CH2:5][CH:6]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2I)[C:13]1=[O:23])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][C:26]=1[C:33]([F:36])([F:35])[F:34].N12CCCN=C1CCCCC2.[O:48]1CCOC[CH2:49]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][CH2:5][CH:6]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:49](=[O:48])[NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[C:26]([C:33]([F:34])([F:35])[F:36])[CH:27]=2)[C:13]1=[O:23])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 485440Benzenemethanamine, 4-chloro-3-(trifluoromethyl)-HCID 86653562HCID 86653562, compound

Product 1

HCID 68347608HCID 68347608, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
110 °C

Procedure

A 5-mL process vial was charged with 2-(5-iodo-1-oxoisoquinolin-2(1H)-yl)propane-1,3-diyl diacetate (200 mg, 0.0004 mol), (4-chloro-3-(trifluoromethyl)phenyl)methanamine (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 yellow oil. MS m/z (M+H) 538.9

Workup

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

Sources & evidence

ORD record
ord-8f03db26e76344c68e33db2a76672308
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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