Methanol → 7-Bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 2090342Notes

Reaction equation

HRID 2090342 reaction equation
I[Si](C)(C)C.[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH3:21])[N:13](C(OC)=O)[CH2:14]2)=[CH:9][CH:8]=1.CO>C(Cl)Cl>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH3:21])[NH:13][CH2:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 59402311HCID 59402311, compound

Product 1

HCID 444054957-Bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Iodotrimethylsilane (0.982 mL, 0.00690 mol, Aldrich, Cat. No. 195529) was added to a solution of methyl 7-bromo-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (490 mg, 0.0017 mol) in methylene chloride (10 mL) and the reaction was stirred at 50° C. for 2 h. The reaction was cooled to r.t. and anhydrous methanol (2 mL) was added. The reaction mixture was stirred for additional 5 min, and the volatiles were removed under reduced pressure. The residue was treated with diethyl ether and filtered. The solid was washed with ether, dried under vacuum to provide the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=226.2.

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. stirringThe reaction mixture was stirred for additional 5 min
  3. customthe volatiles were removed under reduced pressure
  4. additionThe residue was treated with diethyl ether
  5. filtrationfiltered
  6. washThe solid was washed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-94d7b13150fe4d1c80b9e6c88d58487a
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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