Cesium carbonate → HCID 86711904, compound

HRID 1475211Notes

Reaction equation

HRID 1475211 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[C:31]([O-])([O-:33])=[O:32].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:71][N:72]([CH3:76])[CH2:73][CH2:74][NH2:75]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:27][C:24]([F:25])([F:26])[C:31]([O-:33])=[O:32].[CH3:71][NH+:72]([CH3:76])[CH2:73][CH2:74][NH:75][C:2]1[CH:30]=[CH:29][CH:28]=[C:4]([CH2:5][N:6]2[C:10]([CH3:11])=[N:9][C:8]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=4)[N:13]=3)=[N:7]2)[CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66053N,N-DimethylethylenediamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86711906HCID 86711906, compound

Product 1

HCID 86711904HCID 86711904, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

5-(1-(3-Bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (40 mg, 0.0833 mmol), Cs2CO3 (54 mg, 0.167 mmol), XPhos (16 mg, 0.0333 mmol), Pd2(dba)3 (15 mg, 0.0167 mmol), and N′,N′-dimethylethane-1,2-diamine were placed in a microwave reaction vessel and dioxane (1 mL), which had been degassed by bubbling N2 through it for 10 min, was added. The reaction was heated by microwave irradiation at 120° C. for 1 h. Purification by prep-HPLC (MeCN/H2O 30%-70% MeCN containing 0.1% TFA) afforded N,N-dimethyl-2-((3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenyl)amino)ethanaminium trifluoroacetate as a thin film (1.5 mg, 4%). MS (ES+) C23H24F3N7O2 requires: 487. found 488 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.32-8.24 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 7.20-7.15 (m, 1H), 6.63-6.56 (m, 2H), 6.54-6.51 (m, 1H), 5.35 (s, 2H), 3.53 (t, J=5.4 Hz, 2H), 3.28 (t, J=5.4 Hz, 2H), 2.87 (s, 6H), 2.54 (s, 3H).

Workup

  1. customhad been degassed
  2. customby bubbling N2 through it for 10 min
  3. additionwas added
  4. customPurification by prep-HPLC (MeCN/H2O 30%-70% MeCN containing 0.1% TFA)

Sources & evidence

ORD record
ord-9015d06bf712468a87898974d67f2c74
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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