Tetrabutylammonium Fluoride → 3-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

HRID 2059788Notes

Reaction equation

HRID 2059788 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:11]([C:23]([F:26])([F:25])[F:24])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:29]#[C:30][Si](C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:29]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:2]=1[CH3:1])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)=[C:11]([C:23]([F:24])([F:26])[F:25])[CH:10]=1)=[O:7])#[CH:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 689162413-trimethylsilylethynyl-4-methyl-N-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]benzamide

Product 1

HCID 577373983-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethylphenyl]-3-trimethylsilanylethynyl-benzamide (2.0 g, 4.1 mmol) in THF (15 mL) was added 5 mL of TBAF in THF (1.0M). After stirring at rt for 1 h, the mixture was partitioned between H2O and EtOAc. The combined organic layers were dried over Na2SO4, filtered, and then concentrated on a rotavap and the residue was purified on a silica gel column (eluent: 10% MeOH in CH2Cl2, MeOH was presaturated with ammonia gas) to give the desired product as a light yellow solid in 78% yield (1.33 g).

Workup

  1. customthe mixture was partitioned between H2O and EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe residue was purified on a silica gel column (eluent: 10% MeOH in CH2Cl2, MeOH was presaturated with ammonia gas)

Sources & evidence

ORD record
ord-a822d0cf41104883ad2b15898bb4441c
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

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