Azidotrimethylsilane → HCID 178462455, compound

HRID 659612Notes

Reaction equation

HRID 659612 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH:19]([C:23]#[N:24])[CH2:18]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].C[Al](C)C.[Si]([N:33]=[N+:34]=[N-:35])(C)(C)C>C1(C)C=CC=CC=1>[NH:33]1[C:23]([CH:19]2[CH2:20][CH2:21][CH2:22][N:17]([CH2:16][C:12]3[CH:13]=[CH:14][C:15]4[N:3]([CH2:1][CH3:2])[C:4]5[C:9]([C:10]=4[CH:11]=3)=[CH:8][CH:7]=[CH:6][CH:5]=5)[CH2:18]2)=[N:24][N:35]=[N:34]1

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 16682925TrimethylaluminumHCID 67996668HCID 67996668, compound

Product 1

HCID 178462455HCID 178462455, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A 100-mL 3-necked round-bottomed flask was charged with a solution of 1-((9-Ethyl-9H-carbazol-3-yl)methyl)piperidine-3-carbonitrile (700 mg, 2.17 mmol, 1.00 equiv, 98%) in toluene (30 mL). To this solution was add AlMe3 (960 mg, 13.07 mmol, 6.02 equiv, 98%) and TMSN3 (1.52 g, 12.95 mmol, 5.97 equiv, 98%). The resulting mixture was stirred at 80° C. overnight. Upon completion, it was cooled down to room temperature and transferred into a reparatory funnel and extracted with ethyl acetate (3×50 mL). Combined organic layers were with brine and aqueous NaHCO3 (10%). The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude that was purified by preparative HPLC eluted with 1-10% MeOH in DCM affording 3-((3-(1H-tetrazol-5-yl)piperidin-1-yl)methyl)-9-ethyl-9H-carbazole as white solid (85 mg, 16%). LCMS: [M+H]+: 361. 1H NMR (DMSO-d63, 300 MHz) δ 8.15-8.10 (m, 2H), 7.62-7.57 (m, 2H), 7.47-7.43 (m, 2H), 7.22-7.18 (m, 1H), 4.47-4.40 (m, 2H), 3.92-3.82 (m, 2H), 3.26-3.16 (m, 2H), 2.98-2.94 (m, 1H), 2.37-2.31 (m, 1H), 2.04-2.00 (m, 1H), 1.74-1.57 (m, 3H), 1.32 (t, 3H).

Workup

  1. temperatureUpon completion, it was cooled down to room temperature
  2. customtransferred into a reparatory funnel
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude that
  8. customwas purified by preparative HPLC
  9. washeluted with 1-10% MeOH in DCM

Sources & evidence

ORD record
ord-f7c49a59c9314302981509c37ccbe46b
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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