Dichloromethane → HCID 67005759, compound

HRID 562854Notes

Reaction equation

HRID 562854 reaction equation
C[Mg]Br.Br[C:5]1[CH:6]=[C:7]2[C:11](=[N:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.C(Cl)Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[CH2:22]Br>[Cl-].[Cl-].[Zn+2]>[CH3:28][O:27][C:25]1[CH:24]=[C:21]([CH:20]=[C:19]([O:18][CH3:17])[CH:26]=1)[CH2:22][C:9]1[NH:10][C:11]2=[N:12][CH:13]=[CH:5][CH:6]=[C:7]2[CH:8]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 12744903,5-Dimethoxybenzyl BromideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 67005759HCID 67005759, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Into a round bottom flask, under an atmosphere of nitrogen, methylmagnesium bromide (0.16 mL, 1.4 mmol) was added to a solution of 7-azaindole (1) (0.150 g, 1.27 mmol) in anhydrous methylene chloride (12 mL, 0.19 mol), at room temperature. The resulting mixture was stirred at room temperature for one hour before zinc dichloride (0.21 g, 1.5 mmol) was added. After stirring for an additional hour, 3,5-dimethoxybenzyl bromide (4) (0.35 g, 1.5 mmol) was added into the reaction mixture. The reaction was stirred overnight at room temperature before it was quenched with methanol. The mixture was evaporated to dryness, dissolved into ethyl acetate and washed with water. The aqueous portion was neutralized with sodium bicarbonate (s.s.) and extracted with ethyl acetate (3×). Organic portions were combined and washed with 0.1N HCl, dried over anhydrous sodium sulfate and evaporated under reduced pressure. Purification by preparative TLC with 50% ethyl acetate/hexane gave Compound 29 as a yellow powder (15 mg; M+H=269.2, M−H=267.2).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred overnight at room temperature before it
  3. customwas quenched with methanol
  4. customThe mixture was evaporated to dryness
  5. dissolutiondissolved into ethyl acetate
  6. washwashed with water
  7. extractionextracted with ethyl acetate (3×)
  8. washwashed with 0.1N HCl
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated under reduced pressure
  11. customPurification by preparative TLC with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c805e7b891f49cabe9cb66674e75c9c
Source dataset
uspto-grants-2011_11
Patent number
US08067434B2

Reaction notes

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