tert-Butyldimethylsilyl chloride → 3-(Tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinoline

HRID 1620275Notes

Reaction equation

HRID 1620275 reaction equation
[I:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:16][CH2:17][CH3:18])=[N:4][C:3]=1[OH:19].CC(N(C(C)C)CC1C=CC=CC=1)C.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[C:52]([Si:56](Cl)([CH3:58])[CH3:57])([CH3:55])([CH3:54])[CH3:53]>C(Cl)Cl>[Si:56]([O:19][C:3]1[N:4]=[C:5]([CH2:16][CH2:17][CH3:18])[C:6]2[C:11]([C:2]=1[I:1])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:58])[CH3:57]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 16212447N-benzyl-N-propan-2-ylpropan-2-amine;1,4-bis(ethenyl)benzene;styreneHCID 1784402504-Iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol

Product 1

HCID 681823083-(Tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinolineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol CCH 42098-1 (0.60 g, 1.61 mmol) and diisopropylaminomethyl-polystyrene resin (3 mmol/g, 0.80 g, 2.40 mmol) in dry CH2Cl2 (16 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added tert-butylchlorodimethylsilane (267 mg, 1.77 mmol) and the reaction mixture was stirred for 15 min at RT then for 1 h under reflux. After cooling to RT, the reaction mixture was filtered and the filtrate was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 95:5) gave 3-(tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinoline CCH 42098-2 as an off-white solid (0.65 g, 83% yield).

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturefor 1 h under reflux
  3. temperatureAfter cooling to RT
  4. filtrationthe reaction mixture was filtered
  5. washthe filtrate was washed with brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 95:5)

Sources & evidence

ORD record
ord-150ac60ebef54ab6bc8653ba62b52f17
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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