Pyridine, 2-(trimethylstannyl)- → HCID 131718087, compound

HRID 2255098Notes

Reaction equation

HRID 2255098 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][S:29]([C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:31])=[O:30])=[CH:18][CH:17]=1)[C:5]2=[O:36].C[Sn](C)(C)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[N:6]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][S:29]([C:32]([CH3:33])([CH3:34])[CH3:35])(=[O:30])=[O:31])=[CH:20][CH:21]=1)[C:5]2=[O:36]

Participants

5

Reactant 2

HCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 131718088HCID 131718088, compound

Product 1

HCID 131718087HCID 131718087, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.5 g (0.8 mmol) of 6-iodo-2-propyl-3-[(2'-(t-butylsulphonamido)biphen-4-yl)methyl]-quinazolin-4(3H)-one in 3 mL of dry DMF under nitrogen was treated with 0.24 g (1.1 mmol) of 2-trimethylstannylpyridine and 10 mg (0.01 mmol) bis(triphenylphophine)palladium dichloride. The solution was heated at 80°-90° C. for 2 hours to give a black solution. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography over silica gel eluting with 40% EtOAc/hexanes to give the title compound. 1H-NMR (CDCl3, 200 MHz): δ0.98 (s, 9H), 1.06 (t, 3H,), 1.78 (m, 2H), 2.76 (t, 2H,), 5.49 (bs, 2H), 7.29 (m, 7H), 8.50 (m, 8H), 7.75-7.91 (m, 2H), .8.15 (dd,1H), 8.57 (dd, 1H), 8.71 (dm, 1H), 8.82 (d, 1H).

Workup

  1. temperatureThe solution was heated at 80°-90° C. for 2 hours
  2. customto give a black solution
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by flash chromatography over silica gel eluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-2d9d2331376647159c0a87720e5049bc
Source dataset
uspto-grants-1993_08
Patent number
US05238942

Reaction notes

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