Trifluoroacetic acid → 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole

HRID 1174673Notes

Reaction equation

HRID 1174673 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([C:13]3[N:14]=[CH:15][N:16](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:17]=3)O)[C:5]=2[O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C:13]3[NH:14][CH:15]=[N:16][CH:17]=3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 59749547(2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol2×

Product 1

HCID 597495595-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazoleYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) (1 g, 2.11 mmol) in dichloromethane (30 mL) was reacted with TFA: trifluoroacetic acid (5.3 mL, 68 mmol)) and triethylsilane (TES) (2.8 mL, 17 mmol) at rt for 24 h. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) 330 mg (72%).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customquenched with solid NaHCO3
  3. customthe residue was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-2bb5e3a83f934dd1a51e4292b073a90b
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

Loading…