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Tributylvinyltin → HCID 57665494, compound

HRID 2358422
Notes
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Reaction equation

HRID 2358422 reaction equation
[NH2:1][C:2]1[C:23](I)=[CH:22][C:5]([CH2:6][NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[O:9])=[CH:4][C:3]=1[F:25].[CH2:26]([Sn](CCCC)(CCCC)C=C)[CH2:27]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:23]([CH:26]=[CH2:27])=[CH:22][C:5]([CH2:6][NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[O:9])=[CH:4][C:3]=1[F:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 68454898HCID 68454898, compound

Product 1

HCID 57665494HCID 57665494, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To the 50 ml round bottom flask were put 1-(4-amino-3-fluoro-5-iodo-benzyl)-3-(4-t-butyl-benzyl)-urea (0.17 g, 0.37 mmol) and Pd(PPh3)4 (0.05 eq, 21.3 mg). And to this reaction mixture was added 20 ml toluene and tributyl(vinyl)tin (1.1 eq, 0.13 g) by syringe and refluxed for 2 hours. After confirming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, washed with 1M KF solution. And the combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/1).

Workup

  1. temperaturerefluxed for 2 hours
  2. customthe completion of the reaction with TLC
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washwashed with 1M KF solution
  5. dry with materialAnd the combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-0ca584e2e0024a238340dbf005054aa2
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07763657B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes