(Trifluoromethyl)trimethylsilane → HCID 66919619, compound

HRID 1364510Notes

Reaction equation

HRID 1364510 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][C:13]([C:18](=[O:27])[CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([CH3:17])[CH2:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:28][C:29]([F:31])([F:30])[C:18]([C:13]1([CH3:17])[CH:14]=[CH:15][C:16]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=2[CH2:12]1)([OH:27])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilane2×HCID 2724141Tetrabutylammonium FluorideHCID 66919431HCID 66919431, compound

Product 1

HCID 66919619HCID 66919619, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF (1 mL) solution of Example 202 (7 mg, 0.019 mmol) and trifluoromethyl trimethylsilane (28 μL, 6.6 eq) at 0° C. was added a 1 M THF solution of tetrabutylammonium fluoride (128 μL, 6.7 eq). The mixture was slowly warmed to room temperature overnight. HPLC showed only about 10% conversion. Additional trifluoromethyl trimethylsilane (374 μL) was added and the reaction was completed in 1 h. The mixture was concentrated and purified by reverse-phase HPLC (80 to 100% solvent B gradient) to give the title compound (2.4 mg, 29%) as a 1:1 mixture of two isomers. MS found: (M+H)+=431.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by reverse-phase HPLC (80 to 100% solvent B gradient)

Sources & evidence

ORD record
ord-e490d4e7ed264d61994bc0e7a8052b98
Source dataset
uspto-grants-2011_02
Patent number
US07888381B2

Reaction notes

Loading…