Allyl bromide → HCID 68294911, compound

HRID 572525Notes

Reaction equation

HRID 572525 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[CH2:21][C:22]([O:24][CH3:25])=[O:23].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:36](Br)[CH:37]=[CH2:38]>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]([CH2:38][CH:37]=[CH2:36])[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 68295294HCID 68295294, compound

Product 1

HCID 68294911HCID 68294911, 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)acetate (60 mg, 0.179 mmol) in tetrahydrofuran (THF) (2 mL) was treated with LiHMDS (0.358 mL, 0.358 mmol) and allyl bromide (0.232 mL, 2.68 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 1 hour. The mixture was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The material was used crude in the next step (64 mg, 95%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.44-8.54 (m, 1 H) 7.41-7.56 (m, 2 H) 7.06-7.19 (m, 2 H) 6.97-7.05 (m, 1 H) 6.80-6.91 (m, 1 H) 5.40-5.70 (m, 1 H) 4.85-5.06 (m, 2 H) 3.89-4.05 (m, 1 H) 3.68 (s, 3 H) 3.53 (s, 3 H) 2.91-3.06 (m, 1 H) 2.43-2.55 (m, 1 H) 2.41 (s, 3 H) 2.03 (s, 3 H). LC/MS (m/z) ES+=376 (M+1).

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8659468ed7a4eb0be68de7d84862abb
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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