Nitrogen → 3-(2-((Dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 2059796Notes

Reaction equation

HRID 2059796 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]([C:10]2[CH:11]=[C:12]([NH:20]C(=O)C3C=CC(C)=C(C#C[Si](C)(C)C)C=3)[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=2)[CH:7]=[CH:8][N:9]=1)[CH3:3].CN(CC1N(C2C=C(NC(=O)C3C=CC(C)=C(I)C=3)C=C(C(F)(F)F)C=2)C=CN=1)C.N#N.C(N(CC)C(C)C)(C)C.C[Si](C#C)(C)C>[Cu]I.CCOC(C)=O.O.CN(C=O)C>[CH3:3][N:2]([CH2:4][C:5]1[N:6]([C:10]2[CH:11]=[C:12]([CH:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:15]=2)[NH2:20])[CH:7]=[CH:8][N:9]=1)[CH3:1]

Participants

10

Reactant 5

HCID 947NitrogenHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 46838614N-(3(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamideHCID 68920126HCID 68920126, compound

Product 1

HCID 468386103-(2-((Dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potential synthesis of N-[3-{2-[(dimethylamino)methyl]-1H-imidazol-1-yl}-5-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide: N-(3-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide (5 mmol), Pd[(PPh3)]4 (289 mg, 0.25 mmol). CuI (71 mg, 0.375 mmol) are placed in a schlenk flask. The flask is subjected to 3 cycles of vacuum refilling with N2. To this mixture is added anhydrous N,N-diisopropylethylamine (1.1 mL, 6 mmol), DMF (5 mL), and trimethylsilylacetylene (0.92 mL, 6.5 mmol). This solution is stirred at rt for 24 h. Water and EtOAc are added to the reaction mixture to facilitate the extraction. The combined organic layers are dried over Na2SO4, filtered, and then concentrated on a rotavap and the residue is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeOH was pre-saturated with ammonia gas) to give the desired product.

Workup

  1. extractionthe extraction
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe residue is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeOH was pre-saturated with ammonia gas)

Sources & evidence

ORD record
ord-3300ee00b7f64d47ba819bded6246785
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

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