Toluene → 2-(5-Isopropylisochroman-1-yl)-4,5-dihydro-1H-imidazole

HRID 1771419Notes

Reaction equation

HRID 1771419 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.[C:17](P(C(C)(C)C)C(C)(C)C)(C)([CH3:19])[CH3:18].C1(C)C=CC=CC=1.[Br-].C([Zn+])(C)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:17]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 1140TolueneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 717669082-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazoleHCID 178461827HCID 178461827, compound

Product 1

HCID 898518992-(5-Isopropylisochroman-1-yl)-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole (0.25 g, synthesis method A), palladium(II) acetate (0.01 g), tri-tert-butylphosphine (0.044 ml) and toluene (3 ml) in ice bath temperature was added 6.22 ml of 0.5M isopropyl zinc bromide in THF, and stirred at ambient temperature for 3 hrs. The reaction was quenched with dilute hydrochloric acid, and the organic phase was separated. The aqueous phase was made alkaline with 1M NaOH, and purified with separation methods A and G to yield the title compound. (Yield 2 mg).

Workup

  1. customThe reaction was quenched with dilute hydrochloric acid
  2. customthe organic phase was separated
  3. custompurified with separation methods A and G

Sources & evidence

ORD record
ord-e6cd09a571514c8db5ca159af08104ca
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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