O-Xylene → HCID 136175573, compound

HRID 1950034Notes

Reaction equation

HRID 1950034 reaction equation
[C:1]([N:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:19]([F:32])[CH:18]=1)[C:5]1[CH:6]=[C:7]([O:12]C(=O)C)[CH:8]=[CH:9][C:10]=1Br)(=[O:3])[CH3:2].C1(C)C(C)=CC=CC=1.C([Sn](CCCC)(CCCC)[C:46]1[S:47][C:48]2[CH:54]=[CH:53][CH:52]=[CH:51][C:49]=2[N:50]=1)CCC.C(=O)([O-])[O-].[K+].[K+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[S:47]1[C:48]2[CH:54]=[CH:53][CH:52]=[CH:51][C:49]=2[N:50]=[C:46]1[C:10]1[CH:9]=[CH:8][C:7]([OH:12])=[CH:6][C:5]=1[N:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:19]([F:32])[CH:18]=1)[C:1](=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 7237O-XyleneHCID 11430Potassium CarbonateHCID 37623922-(Tributylstannyl)-1,3-benzothiazoleHCID 57934161HCID 57934161, compound

Product 1

HCID 136175573HCID 136175573, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of acetic acid 3-{acetyl-[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-bromophenyl ester (50 mg) and dichlorobis(triphenylphosphine)palladium (II) (7 mg), xylene (1 ml) and 2-tributylstannylbenzothiazole (84 mg) was refluxed for 1.5 hours. The reaction mixture was cooled at room temperature, methanol (2 ml), water (1 ml) and potassium carbonate (50 mg) was added thereto, and the solution was vigourously stirred for 15 minutes at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, then dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (20 mg).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-30fa6d4f8e1e4d2e93465f020c922f81
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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