Ammonium Chloride → 1-Benzyl-4-bromoisoquinoline

HRID 42218

Reaction equation

HRID 42218 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][N:3]=1.[Br-].[CH2:14]([Zn+])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][N:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4597664-Bromo-1-chloroisoquinolineHCID 178419772HCID 178419772, compound

Product 1

HCID 236284181-Benzyl-4-bromoisoquinolineYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

In a 40 mL vial 490 mg (2.00 mmol) 1-chloro-4-bromo-isoquinoline and 40 mg (0.034 mmol) tetrakis(triphenylphosphine)palladium(0) is added to 4 mL THF. After all solids are dissolved, 8 mL of 0.5 M (4.0 mmol) benzyl zinc bromide in THF is slowly added by syringe and the resulting reaction mixture is stirred at 25° C. After 12 hrs, the mixture is poured into cold solution of saturated NH4Cl and extracted with EtOAc. The organic extracts are concentrated in vacuo and the resulting residue is purified by silica chromatography using a heptane/EtOAc gradient. Pure fractions are pooled and evaporated to give 150 mg (0.50 mmol) of the title compound.

Workup

  1. dissolutionAfter all solids are dissolved
  2. customthe resulting reaction mixture
  3. extractionextracted with EtOAc
  4. concentrationThe organic extracts are concentrated in vacuo
  5. customthe resulting residue is purified by silica chromatography
  6. customevaporated

Sources & evidence

ORD record
ord-219230f852f44f51bfb10fb2f15a93bf
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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