Allyltributylstannane → HCID 57786562, compound

HRID 1669061Notes

Reaction equation

HRID 1669061 reaction equation
I[C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][CH2:12]3)=[CH:8][C:6]=2[N:7]=1.[CH2:16]([Sn](CCCC)(CCCC)CCCC)[CH:17]=[CH2:18]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][CH2:12]3)=[CH:8][C:6]=2[N:7]=1)[CH:17]=[CH2:16]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 16081315HCID 16081315, compound

Product 1

HCID 57786562HCID 57786562, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Pd(PPh3)4 (0.89 g, 0.77 mmol) was added to a stirred, degassed solution of iodide 66 (4.80 g, 15.3 mmol) and allyltributyltin (5.2 mL, 16.9 mmol) in DME (100 mL), and the mixture stirred at reflux temperature for 8 h. The solvent was evaporated and the residue purified by chromatography, eluting with 10% EtOAc/pet. ether, to give 1-oxide 69 (2.96 g, 85%) as white solid: mp (EtOAc/pet. ether) 60-61° C.; 1H NMR δ 8.26 (s, 1H, H-9), 7.77 (s, 1H, H-5), 6.12-6.23 (m, 1H, H-2′), 5.29 (dd, J=17.1, 1.5 Hz, 1H, H-3′), 5.22 (dd, J=10.1, 1.3 Hz, 1H, H-3′), 3.77 (br d, J=6.9 Hz, 2H, H-1′), 3.08-3.14 (m, 4H, H-6, H-8), 2.21 (p, J=7.5 Hz, 2H, H-7); 13C NMR δ 164.1, 154.8, 149.0, 147.5, 133.0, 132.3, 122.7, 118.2, 114.3, 41.6, 33.2, 32.8, 25.7. Anal. calcd for C13H13N3O: C, 68.7; H, 5.8; N, 18.5. Found: C, 68.7; H, 5.9; N, 18.7%.

Workup

  1. temperatureat reflux temperature for 8 h
  2. customThe solvent was evaporated
  3. customthe residue purified by chromatography
  4. washeluting with 10% EtOAc/pet. ether

Sources & evidence

ORD record
ord-cf90c2cd189041ef95c8c7544f0de34f
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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