p-Toluenesulfonic acid → HCID 178466251, compound

HRID 1694814Notes

Reaction equation

HRID 1694814 reaction equation
F[C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6](F)[C:3]=1[CH:4]=O.[CH2:13]([NH2:17])[CH2:14]CC.[C:18]1([CH3:28])C=CC(S(O)(=O)=O)=CC=1.[CH2:29]([Mg]Br)[CH3:30].B(Br)(Br)Br.ICC.C(=O)([O-])[O-].[K+].[K+].C([SiH](CC)CC)C.F[C:54](F)(F)C(O)=O.[CH3:60][N:61](C)C=O>C1(C)C=CC=CC=1.O1CCCC1.CCOCC.ClCCl.[Cl-].[Mn+2].[Cl-]>[CH2:11]([O:10][C:9]1[C:2]([CH2:18][CH3:28])=[C:3]([C:6]([CH2:29][CH3:30])=[CH:7][CH:8]=1)[CH2:4][C:14]1[N:61]=[CH:60][NH:17][CH:13]=1)[CH3:54]

Participants

16

Reactant 10

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 6340IodoethaneHCID 6422Trifluoroacetic acidHCID 8007ButylamineHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 25134Boron tribromideHCID 5990732,6-Difluoro-3-methoxybenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 178466251HCID 178466251, compound

Reagents, catalysts & solvents 5

HCID 10313134Manganese(2+) dichlorideCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

Prepared in analogy to Example 72(a)-(e) from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in toluene, then treatment with 3 equivalents of ethylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel, then treatment with boron tribromide in dichloromethane, then treatment with iodoethane and potassium carbonate in N,N-dimethylformamide, then treatment with in situ prepared (1-trityl-1H-imidazol-4-yl)-magnesium halide in dichloromethane, and then treatment with triethylsilane and trifluoroacetic acid in dichloromethane in a pressure tube at 70° C. for 16 h. Amorphous white solid. MS (ISP): 259.3 ([M+H]+).

Sources & evidence

ORD record
ord-43eb5dcb246e4b499a808323ac546612
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

Loading…