Sodium Iodide → (6-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester

HRID 1713097Notes

Reaction equation

HRID 1713097 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6][CH2:5]2.Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[Na+].[Na+].[Na+].[I-]>C(#N)C.O>[C:17]([O:16][C:14](=[O:15])[CH2:13][N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH2:8]1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 158851836-Bromo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 57420571(6-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6-bromo-1,2,3,4-tetrahydro-isoquinoline (10.60 g, 50 mmol) and t-butyl bromoacetate (9.95 g, 51 mmol, 1.02 eq.) in acetonitrile (100 ml) are added sodium carbonate (10.6 g, 100 mmol, 2.0 eq.) and NaI (375 mg, 2.5 mmol, 0.05 eq.). The resulting mixture is stirred at rt for 16 hr. Water (100 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with EtOAc (100 ml×3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by silica gel flash chromatography (EtOAc/hexane, 1:4) to give the title compound. MS (+VE) m/z 326.10 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with EtOAc (100 ml×3)
  5. dry with materialthe combined organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel flash chromatography (EtOAc/hexane, 1:4)

Sources & evidence

ORD record
ord-46a249af3deb471da0bbcf449cd97464
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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