Water → 2[4-(3-bromopropyl)-3-propylphenyl]-6,7-dihydro-5H-pyrano(2,3-d]thiazole

HRID 603513Notes

Reaction equation

HRID 603513 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][O:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13](O)=[C:12]([CH2:17][CH2:18][CH3:19])[CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:26][CH2:27][CH2:28][CH2:29]Br.O>CN(C=O)C>[Br:26][CH2:27][CH2:28][CH2:29][C:13]1[CH:14]=[CH:15][C:10]([C:2]2[S:1][C:5]3[CH2:6][CH2:7][CH2:8][O:9][C:4]=3[N:3]=2)=[CH:11][C:12]=1[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 1363400774-(6,7-dihydro-5H-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenol

Product 1

HCID 670189722[4-(3-bromopropyl)-3-propylphenyl]-6,7-dihydro-5H-pyrano(2,3-d]thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(6,7-dihydro-5H-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenol (560 mg, 2.02 mmol) (Example 505) in DMF (5 mL) were added Cs2CO3 (0.99 g, 3.03 mmol) and 1,3-dibromopropane (0.72 mL, 7.07 mmol). The reaction mixture was stirred at rt for 18 h. Water was added, and the aqueous phase was extracted with Et2O. The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (9:1 hexanes/EtOAc) to give the title compound was a white solid (121 mg, 15%). 1H NMR (400 MHz, CDCl3) 7.68 (d, 1H), 7.65 (dd, 1H), 6.82 (d, 1H), 4.30 (t, 2H), 4.12 (t, 2H), 3.62 (t, 2H), 2.78 (t, 2H), 2.61 (t, 2H), 2.34 (quintet, 2H), 2.11-2.03 (m, 2H), 1.63 (hex, 2H), 0.96 (t, 3H); LC-MS: RT=4.05 min, (M+H)+ 396.3.

Workup

  1. extractionthe aqueous phase was extracted with Et2O
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-7cdff0afec7646ccbe02188b4a91beb3
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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