HCID 10449650, compound → HCID 22716444, compound

HRID 1582886Notes

Reaction equation

HRID 1582886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.C[Sn](C)(C)[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][C:28]([O:34][CH3:35])=[C:27]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:26]=1>C1COCC1.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>[CH2:37]([O:36][C:27]1[C:28]([O:34][CH3:35])=[CH:29][C:30]([N+:31]([O-:33])=[O:32])=[C:25]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[CH:11]3)[CH:26]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 2

HCID 10449650HCID 10449650, compoundHCID 22716430HCID 22716430, compound

Product 1

HCID 22716444HCID 22716444, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0) (200 mg) and cuprous bromide (20 mg) were added to a solution of 6,7-dimethoxy-2-trifluoromethanesulfonyloxy-naphthalene 10 (500 mg, 1.49 mmol) and trimethylnitroarylstannane 38 (950 mg, 2.25 mmol) in THF (40 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 for 2 days. After cooling, THF was evaporated and ethyl acetate (30 mL) was added to the residue. The solution was washed with water. The organic layer was separated and passed through a Celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4), and evaporated in vacuo. The residue was chromatographed using a 70:30 mixture of hexanes:ethyl acetate to give 39 (230 mg) in 35% yield; mp 151-153° C.; IR (KBr) 2962, 1608, 1573, 1508, 1416, 1330, 1275, 1254 cm−1; 1H NMR (CDCl3) δ3.98 (3H, s), 3.99 (3H, s), 4.01 (3H, s), 5.20 (2H. s), 6.94 (1H, s), 7.10 (1H, s), 7.14 (1H, s), 7.18 (1H, dd, J1=8.4, J2=1.8), 7.36-7.43 (5H, m), 7.54 (1H, d, J=1.5), 7.56 (1H, s), 7.68 (1H, d, J=8.3); 13C NMR δ56.37, 56.95, 71.69, 106.69, 106.99, 108.67, 116.35, 124.91, 125.78, 127.00, 128.00, 128.87, 129.00, 129.23, 129.53, 131.81, 134.49, 136.15, 141.89, 148.95, 150.41, 151.85; HRMS (EI) calcd for C26H23NO6 m/z: 445.1525; found: 445.1355.

Workup

  1. temperatureThe mixture was then refluxed under N2 for 2 days
  2. temperatureAfter cooling
  3. customTHF was evaporated
  4. additionethyl acetate (30 mL) was added to the residue
  5. washThe solution was washed with water
  6. customThe organic layer was separated
  7. customto remove
  8. washThe organic layer was then washed with brine
  9. dry with materialdried (anhydrous Na2SO4)
  10. customevaporated in vacuo
  11. customThe residue was chromatographed
  12. additiona 70:30 mixture of hexanes

Sources & evidence

ORD record
ord-bf55ac05cdf4413b9641d2f0f25126d1
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

Loading…