Sodium Bicarbonate → HCID 178464138, compound

HRID 1170427Notes

Reaction equation

HRID 1170427 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C@H:4]1[CH2:7][C@H:6]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:14]=[C:15]([I:18])[CH:16]=3)[C:11](=[O:23])[C:10]2=[O:24])[CH2:5]1)[CH3:2].[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[Mg]I.C(=O)(O)[O-].[Na+]>O1CCCC1.CCOCC>[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[C:11]1([OH:23])[C:12]2[C:17](=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[C:19]([F:21])([F:20])[F:22])[N:9]([CH2:8][C@H:6]2[CH2:5][C@H:4]([N:3]([CH2:1][CH3:2])[CH2:25][CH3:26])[CH2:7]2)[C:10]1=[O:24]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 178464130HCID 178464130, compoundHCID 178478195HCID 178478195, compound

Product 1

HCID 178464138HCID 178464138, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 1-1 (3.13 g, 6.52 mmol) in tetrahydrofuran (65 mL) was added dropwise a solution of 2,4-dichlorophenylmagnesium iodide (9.78 mmol) in ether (19.6 mL) at −78° C. The mixture was stirred for 1 hour, and to the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then evaporated. The residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1 to 10/1 to 5/1) to give the titled compound (2.95 g, 86%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1 to 10/1 to 5/1)

Sources & evidence

ORD record
ord-6ad9ea33d20843e893466316899b0344
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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