Tetrahydrofuran → HCID 15030169, compound

HRID 1647616Notes

Reaction equation

HRID 1647616 reaction equation
BrC[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:17][CH:16]=2)=O)[CH:6]=[CH:7][CH:8]=1.C[Sn](C)(C)C1[S:39][CH:40]=[CH:41][N:42]=1.[O:45]1CC[CH2:47][CH2:46]1>CCOCC.Cl[Pd]Cl>[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][N:12]([C:10]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:4][C:3]3[S:39][CH:40]=[CH:41][N:42]=3)[CH:9]=2)[C:46](=[O:45])[CH3:47])=[CH:20][CH:19]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 129566412-(Trimethylstannyl)-1,3-thiazoleHCID 867453663-(bromomethyl)phenyl-N-[2-[4-(tetradecyloxy)phenyl]ethyl]acetamide

Product 1

HCID 15030169HCID 15030169, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.3 g of N-[3-(bromomethyl)phenyl-N-[2-[4-(tetradecyloxy)phenyl]ethyl]acetamide, 787.04 mg of 2-(trimethylstannyl)thiazole and 83.77 mg of PdCl2 (PO3)2 in 30 ml of tetrahydrofuran is stirred at reflux for 14 hours. The mixture is diluted with ether and filtered through a pad of silica gel. The filtrate is washed with 1N sodium hydroxide, dried and filtered through a pad of alumina. The solvent is evaporated and the residue chromatographed on silica gel using 1:1 ethyl acetate:hexane to give 0.7 g of the desired product as an oil which crystallized to an off-white solid, m.p. 46°-50° C.

Workup

  1. temperatureat reflux for 14 hours
  2. filtrationfiltered through a pad of silica gel
  3. washThe filtrate is washed with 1N sodium hydroxide
  4. customdried
  5. filtrationfiltered through a pad of alumina
  6. customThe solvent is evaporated
  7. customthe residue chromatographed on silica gel using 1:1 ethyl acetate

Sources & evidence

ORD record
ord-99a39effd5d74f6db975eca03def1f1a
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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