Methanol → HCID 12085947, compound

HRID 397080Notes

Reaction equation

HRID 397080 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:29])([F:28])[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[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=1)=[O:8].CO>C(Cl)Cl>[F:29][C:6]([F:5])([F:28])[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[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 12085946HCID 12085946, compound

Product 1

HCID 12085947HCID 12085947, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (0.49 ml, 0.49 mmol) was added slowly to a solution of 2,2,2-trifluoro-1-[1-(4-iodophenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (0.150 g, 0.33 mmol) in anhydrous CH2Cl2 (10 ml) at 0° C. under N2. The reaction mixture was stirred at 0° C. for 1 hr, then warmed to rt and stirred at rt for 19 hr. MeOH (10 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to a yellow oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 0.121 g (83% yield) of yellow solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 19 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo to a yellow oil
  5. customPurification by flash chromatography
  6. washeluting with hexane:EtOAc (8:2)

Sources & evidence

ORD record
ord-e6e703a2031d4429a42c7509a6483374
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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