Trifluoroacetic acid → HCID 89601857, compound

HRID 526302Notes

Reaction equation

HRID 526302 reaction equation
O[CH:2]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]2[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:14]=12)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:26][N:23]1[CH2:24][CH2:25][C:14]2=[C:13]([CH2:2][C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=3)[C:21]3[C:16]([N:15]2[CH2:22]1)=[CH:17][CH:18]=[CH:19][CH:20]=3

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 89601758HCID 89601758, compound

Product 1

HCID 89601857HCID 89601857, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(hydroxy(2-methyl-1,2,3,4-tetrahydropyrimido[1,6-a]indol-5-yl)methyl)benzoate (80 mg) and Et3SiH (0.5 mL) in 5 mL of CH2Cl2 was added 0.1 mL of TFA. After stirring for 10 min at r.t., the reaction mixture was poured into 15 mL of saturated aqueous solution of NaHCO3 and the mixture was extracted with 2×20 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with up to 100% EtOAc/hexanes to give 70 mg of the title product as white solid.

Workup

  1. extractionthe mixture was extracted with 2×20 mL of EtOAc
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with up to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-857f8d051ad24f8bb592cadbf3c4b44a
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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