Sodium Hydroxide → HCID 178482639, compound

HRID 493491Notes

Reaction equation

HRID 493491 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH3:32])[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[O:21])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]#[N:11].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]([CH3:32])[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[O:21])=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[NH:35][N:34]=[N:33][N:11]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 68862639N-{[3'-bromo-4'-(cyanomethoxy)-1,1'-biphenyl-4-yl]methyl}-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 178482639HCID 178482639, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-N,1-dimethyl-1H-indole-3-carboxamide (2.0 g, 4.1 mmol), prepared in the previous step, sodium azide (0.80 g, 12.3 mmol) and ammonium chloride (0.66 g, 12.3 mmol) in 42 mL of DMF was stirred under nitrogen at 100° C. for 4 h. By TLC a small amount of starting material remained. An additional 0.80 g (12.3 mmol) of sodium azide and 0.66 g (12.3 mmol) of ammonium chloride were added and the reaction stirred at 100° C. for 3 h. After cooling to room temperature the reaction was diluted with 65 mL of water, made basic by the addition of 1 N NaOH and extracted three times with ethyl acetate. The aqueous layer was acidified with 1 N HCl. An oil separated which eventually solidified. The solid was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (1.6 g, 73%) as a tan solid, mp 239° C. Elemental Analysis for C26H23BrN6O2Calc'd: C, 58.77; H, 4.36; N, 15.81. Found: C, 57.73; H, 4.40; N, 15.52

Workup

  1. stirringthe reaction stirred at 100° C. for 3 h
  2. temperatureAfter cooling to room temperature the reaction
  3. extractionextracted three times with ethyl acetate
  4. customAn oil separated which
  5. filtrationThe solid was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3605605259974db4bcafd5173c187e5e
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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