1,4-Dioxane → HCID 58188114, compound

HRID 1845248Notes

Reaction equation

HRID 1845248 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4](I)[CH:3]=1.[CH3:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=1.N12CCCN=C1CCCCC2.[O:34]1CCOC[CH2:35]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1)[C:35]([NH:22][CH2:21][C:18]1[CH:19]=[N:20][C:15]([CH3:14])=[CH:16][CH:17]=1)=[O:34]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27611691-bromo-3-iodo-5-(trifluoromethoxy)benzeneHCID 12214337(6-Methylpyridin-3-yl)methanamine

Product 1

HCID 58188114HCID 58188114, compound

Reagents, catalysts & solvents 2

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

Procedure

A 5 mL microwave vial was charged with 1-bromo-3-iodo-5-(trifluoromethoxy)benzene (98 mg, 0.27 mmol), (6-methylpyridin-3-yl)methanamine (50 mg, 0.41 mmol), molybdenum hexacarbonyl (160 mg, 0.61 mmol), palladium acetate (8 mg, 0.036 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (120 mg, 0.79 mmol), and 1,4-dioxane (2 mL). The vial was sealed under nitrogen and the reaction was subjected to microwave irradiation at 120° C. for 20 minutes. After cooling, the mixture was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 391.2 [M+1]+; 1H NMR (CDCl3, 400 MHz): 8.43 (d, J=2.1 Hz, 1H), 7.85 (t, J=1.5 Hz, 1H), 7.63-7.61 (m, 2H), 7.52 (s, 1H), 7.16 (d, J=8.0 Hz, 1H), 6.74 (br, 1H), 4.60 (d, J=5.8 Hz, 2H), 2.55 (s, 3H).

Workup

  1. customThe vial was sealed under nitrogen
  2. customirradiation at 120° C. for 20 minutes
  3. temperatureAfter cooling
  4. customthe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-29147acebbec4ad09de7fa11e7cdab62
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…