Methanol → HCID 18172409, compound

HRID 397083Notes

Reaction equation

HRID 397083 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:27])([F:26])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[CH:10]1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:8].CO>C(Cl)Cl>[F:27][C:6]([F:5])([F:26])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[CH:10]1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18172472HCID 18172472, compound

Product 1

HCID 18172409HCID 18172409, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (0.66 ml, 0.66 mmol) was added slowly to a solution of 2,2,2-trifluoro-1-(6-methoxy-1-thiophen-2-yl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone (0.150 g, 0.439 mmol) in anhydrous CH2Cl2 (10 ml) at 0° C. under N2. The resulting red solution was stirred at 0° C. for 30 min, then warmed to rt and stirred at rt for 20 hr. MeOH (5 ml) was slowly added to the reaction mixture with stirring and the resulting solution was concentrated in vacuo to give 0.138 g of a black residue. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 0.006 g (4% yield) of white solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 20 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-825f8bddc6434afaab63c58fcbf11522
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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