Dimethylformamide → HCID 67299344, compound

HRID 1958687Notes

Reaction equation

HRID 1958687 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.Br[CH2:26][CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:26][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 67299495HCID 67299495, compound

Product 1

HCID 67299344HCID 67299344, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

4.8 g of the compound obtained in stage 16E), 3.6 g of 2-(3-bromopropoxy)tetrahydro-2H-pyran and 2.2 g of potassium carbonate are added to 30 ml of DMF and then the mixture is heated at 60° C. for 7 hours. It is poured onto ice-cold water, extraction is carried out with ether and the extract is dried and concentrated to dryness. After purifying by chromatography on silica (heptane and then heptane/AcOEt: 90/10), 6.2 g of the expected compound are obtained.

Workup

  1. additionIt is poured onto ice-cold water, extraction
  2. customthe extract is dried
  3. concentrationconcentrated to dryness
  4. customAfter purifying by chromatography on silica (heptane

Sources & evidence

ORD record
ord-ab15706bbf2d4006accdfa6385e24054
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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