Sodium Hydroxide → HCID 178482587, compound

HRID 1357263Notes

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]([CH3:36])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=1)=[O:19])=[CH:7]2.[N-:37]=[N+:38]=[N-:39].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:39][N:38]=[N:37][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:36])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:21]=1)=[O:19])=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-benzyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.7725 g, 1.44 mmol), prepared in the previous step, sodium azide (0.28 g, 4.3 mmol) and ammonium chloride (0.23 g, 4.3 mmol) in 15 mL DMF was stirred under nitrogen for 4 h at 100° C. The reaction was diluted with water, made basic with 1N NaOH, and extracted five times with ethyl acetate. The ethyl acetate layer was acidified with 1N HCl and the solvent was removed under reduced pressure to give 0.133 g of the desired compound as an off-white solid. The aqueous layer was acidified with 1N HCl. The solution sat at room temperature for 18 h (overnight). A solid had precipitated from solution and was collected by filtration, rinsed with water, and dried under reduced pressure to give the title compound (0.4962 g, 60%) as an off white solid, mp 197-198° C.

Workup

extractionextracted five times with ethyl acetate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-9671eb82525842458cf3fd33140e1617
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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