1,3-Dibromopropane → HCID 69702821, compound

HRID 895372Notes

Reaction equation

HRID 895372 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([NH:11][C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].Br[CH2:28][CH2:29][CH2:30]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:1]([O:3][C:4]([C:5]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:30][CH2:29][CH2:28][N:11]1[C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:26])[CH3:2]

Participants

4

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 69703211HCID 69703211, compound

Product 1

HCID 69702821HCID 69702821, compoundYield 72%

Conditions

Temperature
55 °C

Procedure

2-[6-(4-Iodo-phenoxy)-pyridin-3-ylamino]-malonic acid diethyl ester (4.35 grams, 9.25 mmol) was added to a flame dried flask and dissolved in dimethylformamide (90 mL). 1,3 dibromopropane (938 μL, 9.25 mmol) and cesium carbonate (6 grams, 18.5 mmol) were added and the reaction mixture was stirred for approximately 24 hours to 48 hours. The solution was filtered through celite, and then concentrated under vacuum while heating to 55° C. to remove the dimethylformamide (azeotroping with toluene). The crude product obtained was chromatographed on silica gel (ISCO MPLC purification, 40 minutes, 0-50% ethyl acetate gradient, Biotage flash 40 m column) to provide 3.39 grams (72%) of the title compound. MS m/z: ESI+ 511.1 (M+H)+.

Workup

  1. customdried flask
  2. dissolutiondissolved in dimethylformamide (90 mL)
  3. filtrationThe solution was filtered through celite
  4. concentrationconcentrated under vacuum
  5. customto remove the dimethylformamide (azeotroping with toluene)
  6. customThe crude product obtained
  7. customwas chromatographed on silica gel (ISCO MPLC purification, 40 minutes, 0-50% ethyl acetate gradient, Biotage flash 40 m column)

Sources & evidence

ORD record
ord-d2df5d75e4c148c5b671463372cd8fe2
Source dataset
uspto-grants-2005_07
Patent number
US06916807B2

Reaction notes

Loading…