Iodoethane → HCID 68295573, compound

HRID 572528Notes

Reaction equation

HRID 572528 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[CH:21]([OH:26])[C:22]([O:24][CH3:25])=[O:23].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:38][CH3:39]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[CH:21]([O:26][CH2:38][CH3:39])[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 68295591HCID 68295591, compound

Product 1

HCID 68295573HCID 68295573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)-2-hydroxyacetate (50 mg, 0.142 mmol) in Tetrahydrofuran (THF) (1 mL) was treated with LiHMDS (0.213 mL, 0.213 mmol) and iodoethane (0.069 mL, 0.854 mmol) at 0° C. The mixture was stirred at room temperature for 1 hour and then quenched with saturated NH4Cl solution. The mixture was extracted with ethyl acetate, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The residue was used crude in the next step without further purification (44 mg, 82%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.47-8.55 (m, 1 H) 7.46-7.55 (m, 2 H) 7.06-7.21 (m, 3 H) 6.85-6.96 (m, 1 H) 4.87-4.98 (m, 1 H) 3.65-3.68 (m, 2 H) 3.66 (s, 3 H) 2.86-3.00 (m, 3 H) 2.42 (s, 3 H) 2.02 (s, 3 H) 1.10-1.24 (m, 3 H). LC/MS (m/z) ES+=380 (M+1).

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwithout further purification (44 mg, 82%)

Sources & evidence

ORD record
ord-5ae0b6dc0f7542d3aad96ec37b0785b1
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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