2-(Tributylstannyl)furan → 7-[3-(2-Furyl)phenoxy]-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

HRID 851887Notes

Reaction equation

HRID 851887 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]2[N:10]3[CH2:18][CH2:17][CH2:16][C:11]3=[N:12][S:13](=[O:15])(=[O:14])[C:8]=2[CH:7]=1.C([Sn](CCCC)(CCCC)[C:29]1[O:30][CH:31]=[CH:32][CH:33]=1)CCC>C1(C)C=CC=CC=1>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]2[N:10]3[CH2:18][CH2:17][CH2:16][C:11]3=[N:12][S:13](=[O:15])(=[O:14])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 694145897-(3-bromophenoxy)-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

Product 1

HCID 694146437-[3-(2-Furyl)phenoxy]-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of the product obtained in Step A (200 mg, 0.50 mmol), 222 μl (0.66 mmol) of 2-(tributylstannyl)furan and 30 mg (0.025 mmol) of tetrakistriphenylphosphine in 4 ml of toluene is refluxed for 45 minutes. The toluene is evaporated off in vacuo and the residue is chromatographed on SiO2 (CH2Cl2/acetone 96/4) to yield the title product.

Workup

  1. temperatureis refluxed for 45 minutes
  2. customThe toluene is evaporated off in vacuo
  3. customthe residue is chromatographed on SiO2 (CH2Cl2/acetone 96/4)

Sources & evidence

ORD record
ord-6a982e73ef2243a795097b4f841f666c
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

Loading…