2-(Tributylstannyl)-1,3-thiazole → HCID 135840838, compound

HRID 1274160Notes

Reaction equation

HRID 1274160 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH:5]([CH3:14])[CH2:6][C:7]2=[O:13].C([Sn](CCCC)(CCCC)[C:20]1[S:21][CH:22]=[CH:23][N:24]=1)CCC>O1CCOCC1.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>[OH:12][C:9]1[CH:10]=[CH:11][C:2]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[C:3]2[C:8]=1[C:7](=[O:13])[CH2:6][CH:5]([CH3:14])[CH2:4]2

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 221203955-Bromo-3,4-dihydro-8-hydroxy-3-methyl-1(2H)-naphthalenone

Product 1

HCID 135840838HCID 135840838, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-bromo-8-hydroxy-3-methyl-1,2,3,4-tetrahydronaphthalen-1-one (3.0 g, 0.012 mol) and 2-(tri-n-butylstannyl)thiazole (6.4 g, 0.17 mol) in dioxan (100 mL) was degassed with nitrogen for 30 min. Tetrakis(triphenylphosphine)palladium(0) (1 g) was added and the mixture heated at reflux for 48 h. The solvent was evaporated and the residue chromatographed on silica gel, eluting with EtOAc:hexane (1:4). The title compound (1.9 g, 62%) was isolated as a yellow oil. 1H NMR (360 MHz, CDCl3) δ 1.13 (3H, d, J=6.5 Hz), 2.20-2.34 (1H, m), 2.39-2.47 (1H, m), 2.73-2.83 (2H, m), 3.34-3.49 (1H, m), 6.90 (1H, d, J=8.8 Hz), 7.40 (1H, d, J=3.3 Hz), 7.73 (1H, d, J=8.8 Hz), 7.89 (1H, d, J=3.3 Hz), 12.93 (1H, s). MS (ES+) 260 (M+1).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was evaporated
  4. customthe residue chromatographed on silica gel
  5. washeluting with EtOAc:hexane (1:4)

Sources & evidence

ORD record
ord-03e3493c0b7145b3b721b806103792da
Source dataset
uspto-grants-2000_12
Patent number
US06156761

Reaction notes

Loading…