Sodium Azide → HCID 22941955, compound

HRID 361593Notes

Reaction equation

HRID 361593 reaction equation
C(O[CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[C:14](/[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[CH:15]/[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:9]=1)(=O)C.[N-:29]=[N+:30]=[N-:31].[Na+]>C1COCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:17]1([CH2:16]/[CH:15]=[C:14](/[C:10]2[N:9]=[C:8](/[CH:7]=[CH:6]/[CH2:5][N:29]=[N+:30]=[N-:31])[CH:13]=[CH:12][CH:11]=2)\[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18659963HCID 18659963, compound

Product 1

HCID 22941955HCID 22941955, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-en-1-yl acetate (136 mg, 0.365 mmol) in a mixture of THF/water (5:1, 5 ml) was treated with sodium azide (28 mg, 0.44 mmol) and tetrakis(triphenylphosphine) palladium(0) (17 mg, 0.015 mmol). The reaction was stirred at room temperature for 18 hours. Solvent was removed under reduced pressure to leave a dark brown residue. The product was purified by column chromatography on silica-gel eluting with 5% methanol/DCM. Product containing fractions were combined and solvent removed under reduced pressure to yield {3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-enyl}-azide as a brown gum (110 mg, 85%). 1H-NMR; δ (CDCl3), 7.67 (1H, m), 7.56 (1H, m), 7.40 (2H, m), 7.24 (2H, d, J=8.2 Hz), 7.19 (1H, t, J=6.8 Hz), 7.10 (2H, m), 6.91 (1H, dt, J=15.8, 6.6 Hz), 6.73 (2H, m), 4.02 (2H, d, J=8.8 Hz), 3.35 (2H, m), 2.70 (2H, m), 2.41 (3H, s) and 1.82 (4H, m).

Workup

  1. customSolvent was removed under reduced pressure
  2. customto leave a dark brown residue
  3. customThe product was purified by column chromatography on silica-gel
  4. washeluting with 5% methanol/DCM
  5. additionProduct containing fractions
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-ba98c721e69441aa97b58228b5952969
Source dataset
uspto-grants-1999_02
Patent number
US05866588

Reaction notes

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