Azidotrimethylsilane → HCID 70564996, compound

HRID 1427255Notes

Reaction equation

HRID 1427255 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[C:9]#[CH:10])=[CH:4][CH:3]=1.C[Si]([N:34]=[N+:35]=[N-:36])(C)C>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([C:11]2[CH:12]=[N:36][NH:35][N:34]=2)[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 86705046HCID 86705046, compound

Product 1

HCID 70564996HCID 70564996, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of tert-butyl 1-(3-(4-chlorophenyl)pent-1-yn-3-yl)-1H-indol-4-ylcarbamate (200 mg, 0.5 mmol) in trimethylsilyl azide (3 mL) was heated at 100° C. under microwave for 3 h. The resulting mixture was diluted with brine (10 mL) and extracted with EA. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and the solvent was removed in vacuo to afford the crude product. The product was purified via column chromatography (75% EtOAc/hexanes) to provide the title product.

Workup

  1. extractionextracted with EA
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customto afford the crude product
  6. customThe product was purified via column chromatography (75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6e75f7f6d1ee457791b727a138e1897f
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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