Chloride → HCID 178441200, compound

HRID 1357273Notes

Reaction equation

HRID 1357273 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:34])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[C:21]=1[CH2:30][CH2:31][CH2:32][CH3:33])=[O:19])=[CH:7]2.[N-:35]=[N+:36]=[N-:37].[Na+].[Cl-].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:37][N:36]=[N:35][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:34])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[C:21]=1[CH2:30][CH2:31][CH2:32][CH3:33])=[O:19])=[CH:7]2

Participants

7

Reactant 4

HCID 312ChlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 12083573HCID 12083573, compound

Product 1

HCID 178441200HCID 178441200, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.79 g, 3.45 mmol), prepared in the previous step, sodium azide (673 mg, 10.35 mmol) and ammoniun chloride (554 mg, 10.36 mmol) in 100 mL of DMF was stirred under nitrogen at 100° C. for 4.25 h. The reaction was diluted with water, made basic by the addition of 20 mL of 1 N NaOH and extracted multiple times with ethyl acetate. The aqueous layer was acidified with 40 mL of 1 N HCl. A brown oil separated. The oil was partitioned between the aqueous layer and methylene chloride. The organic layer separated and the aqueous layer was extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in 20 mL of 1 N NaOH and then acidified with 30 mL 1 N HCl. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (1.75 g, 89%) as an off-white solid, mp 147-149° C.

Workup

  1. extractionextracted multiple times with ethyl acetate
  2. customA brown oil separated
  3. customThe oil was partitioned between the aqueous layer and methylene chloride
  4. customThe organic layer separated
  5. extractionthe aqueous layer was extracted three times with methylene chloride
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent removed under reduced pressure
  8. dissolutionThe residue was dissolved in 20 mL of 1 N NaOH
  9. customThe solid that formed
  10. filtrationwas collected by filtration
  11. washrinsed with water
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-0e2450682d824f02b85223fca2538083
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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