Triphenylphosphine → HCID 57794658, compound

HRID 2099803Notes

Reaction equation

HRID 2099803 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH:8][C:9](=O)[CH:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([CH3:21])[CH:20]=1)[NH:17][N:16]=[CH:15]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si](N=[N+]=[N-])(C)C>O1CCCC1>[C:25]([O:24][C:23](=[O:29])[NH:22][CH:10]([C:9]1[N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[N:7][N:8]=1)[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([CH3:21])[CH:20]=1)[NH:17][N:16]=[CH:15]2)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 57794718HCID 57794718, compound

Product 1

HCID 57794658HCID 57794658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1-{2-(pyridin-2-yl)hydrazinyl}-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-ylcarbamate (70 mg, 0.17 mmol), triphenylphosphine (54 mg, 0.2 mmol), and trimethylsilyl azide (25 μL, 0.19 mmol) were combined in dry tetrahydrofuran (2.0 mL) at 0° C. Diethylazodicarbaoxylate (33 μL, 0.2 mmol) was added to the reaction mixture to afford a brown solution which was stirred at room temperature for 2 h. The solvents were removed in vacuo and the crude mixture purified by column chromatography to afford 45.2 mg (71%). Mass spec.: 393.04 (MH)+.

Workup

  1. additionwas added to the reaction mixture
  2. customto afford a brown solution which
  3. customThe solvents were removed in vacuo
  4. customthe crude mixture purified by column chromatography
  5. customto afford 45.2 mg (71%)

Sources & evidence

ORD record
ord-4dab9e03927a4de5a31d8adb126aed7d
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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