3-Bromo-2-methyl-1-propene → HCID 68295255, compound

HRID 572527Notes

Reaction equation

HRID 572527 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.Br[CH2:37][C:38]([CH3:40])=[CH2:39]>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]([CH2:39][C:38]([CH3:40])=[CH2:37])[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 2733832Lithium HexamethyldisilazideHCID 68295294HCID 68295294, compound

Product 1

HCID 68295255HCID 68295255, 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 (0.447 mL, 0.447 mmol, 1.0M in THF) and 3-bromo-2-methylpropene (0.271 mL, 2.68 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 and brine, dried over Na2SO4, filtered and concentrated. The residue was used crude in the next step (65 mg, 94%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.43-8.56 (m, 1 H) 7.40-7.57 (m, 2 H) 7.09-7.20 (m, 1 H) 6.95-7.08 (m, 2 H) 6.78-6.86 (m, 1 H) 4.68-4.75 (m, 1 H) 4.44-4.54 (m, 1 H) 3.91-4.03 (m, 1 H) 3.68 (s, 3 H) 3.53 (s, 3 H) 2.40 (br. s., 3 H) 2.04 (s, 3 H) 1.59-1.68 (m, 2 H) 1.49 (br. s., 3 H). LC/MS (m/z) ES+=390 (M+1).

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-169011fa6bb449548a7290733e2fe95c
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

Loading…