Dimethyl Sulfide → 2-(7-Bromo-3-isoquinolinyl)ethanol

HRID 551540Notes

Reaction equation

HRID 551540 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH2:11][CH2:12][OH:13])=[CH:5]2.CSC.C(=O)(O)[O-].[Na+].[OH-].[NH4+:23]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8]([CH:7]=[C:6]([CH2:11][CH2:12][OH:13])[N:23]=[CH:5]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 14923Ammonium HydroxideHCID 516892Sodium BicarbonateHCID 671042662-(5-bromo-1H-inden-2-yl)ethanol

Product 1

HCID 210439272-(7-Bromo-3-isoquinolinyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 52D (0.85 g, 3.5 mmol) in methanol (15 mL) at −70° C. was ozonated until a bluish color developed (˜10 minutes). The mixture was treated with dimethylsulfide (0.7 mL, excess) and sodium bicarbonate (0.2 g) and allowed to warm to room temperature. After stirring for 3 hours, the mixture was treated with aqueous ammonium hydroxide (7.4 mL, 28%). After stirring an additional 4 hours, the reaction mixture was concentrated under vacuum and then diluted with dichloromethane (20 mL). The organic layer was separated and evaporated to provide the title compound which was used without further purification in the next step. 1H NMR (CDCl3) δ 3.13 (t, J=5.6 Hz, 2H); 4.07 (t, J=5.6 Hz, 2H); 7.47 (s, 1H); 7.61 (d, J=8.7 Hz, 1H); 7.71 (dd, J=1.9, 8.7 Hz, 1H); 9.04 (s, 1H); Anal. Calcd. for C11H10BrNO: C, 52.41; H, 4.00; N, 5.56. Found: C, 52.51; H, 3.94; N, 5.42.

Workup

  1. customat −70° C.
  2. custom(˜10 minutes)
  3. stirringAfter stirring an additional 4 hours
  4. concentrationthe reaction mixture was concentrated under vacuum
  5. additiondiluted with dichloromethane (20 mL)
  6. customThe organic layer was separated
  7. customevaporated

Sources & evidence

ORD record
ord-4dea9733179a44348ac750585b9caa8a
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

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