2-Formyl-4-(tributylstannyl)thiazole → 4-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehyde

HRID 2215713Notes

Reaction equation

HRID 2215713 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21](I)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:31]1[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=1)CCC>O1CCOCC1.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>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:31]4[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 164271112-Formyl-4-(tributylstannyl)thiazoleHCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

Product 1

HCID 219519814-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehydeYield 44%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (2 g, 4.56 mmol), 4-(tributylstannyl)thiazole-2-carbaldehyde (1.84 g, 4.56 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.74 g, 20 mol %) heated at reflux overnight (18 hrs) in dioxane (50 ml). The cooled solution was filtered through a plug of Celite®, concentrated and triturated with iso-hexane (3×20 ml). The resultant solid was purified via flash column chromatography on silica gel, eluting with 5% methanol in chloroform. The purified product was isolated as a yellow solid (0.85 g, 44%). δH [2H6] DMSO 10.10(1H,s), 9.30(1,bs), 8.90(1Hs), 8.50(2H,s&d), 8.45(1H,d), 8.20(1H,d), 7.40(5H,bm), 7.10(4H,2d), 6.80(1H,d).

Workup

  1. customPrepared
  2. temperatureheated
  3. filtrationThe cooled solution was filtered through a plug of Celite®
  4. concentrationconcentrated
  5. customtriturated with iso-hexane (3×20 ml)
  6. customThe resultant solid was purified via flash column chromatography on silica gel
  7. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-81cebef18e834278850c8eace8736e76
Source dataset
uspto-grants-2006_09
Patent number
US07109333B2

Reaction notes

Loading…