Water → HCID 178464147, compound

HRID 1170443Notes

Reaction equation

HRID 1170443 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:34][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])[C:17]2[C:12](=[CH:13][C:14](I)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33].[OH2:42]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:34][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])[C:17]2[C:12](=[CH:13][C:14]([C:4]3[O:42][CH:7]=[CH:2][CH:3]=3)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33]

Participants

4

Reactant 2

HCID 962WaterHCID 178464149HCID 178464149, compound

Product 1

HCID 178464147HCID 178464147, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the compound of Example 14-1 (140 mg, 0.188 mmol), 2-tributyltinfuran (80 mg, 0.224 mmol) and tetrakistriphenylphosphine palladium (20 mg, 0.017 mmol) in toluene (5 mL) was stirred at 100° C. under nitrogen for 3 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate, and then the organic layer was washed with saturated saline, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (chloroform/methanol=20/1) to give the titled compound (80 mg, 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-7839f3b6a0a6465caed6e44dd779868b
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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