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

HRID 2059797Notes

Reaction equation

HRID 2059797 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)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(C#C[Si](C)(C)C)C=3)C=C(C(F)(F)F)C=2)C=CN=1)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[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

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 68920126HCID 68920126, compoundHCID 86631106HCID 86631106, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potential synthesis of N-[3-{2-[(dimethylamino)methyl]-1H-imidazol-1-yl}-5-(trifluoromethyl)phenyl]-3-ethynyl-4-methylbenzamide: To a solution of N-[3-{2-[(dimethylamino)methyl]-1H-imidazol-1-yl}-5-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide (4.1 mmol) in THF (15 mL) is added 5 mL of TBAF in THF (1.0M). After stirring at rt for 1 h, the mixture is partitioned between H2O and EtOAc. 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: 10% MeOH in CH2Cl2, MeOH was pre-saturated with ammonia gas) to give the desired product.

Workup

  1. customthe mixture is partitioned between H2O and EtOAc
  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: 10% MeOH in CH2Cl2, MeOH was pre-saturated with ammonia gas)

Sources & evidence

ORD record
ord-29338c6b987b44aebe6c5ff08ce6af63
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

Loading…