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Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silane → Ammonia

HRID 73309
Notes
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Reaction equation

HRID 73309 reaction equation
[C:1]([Si:5]([CH3:25])([CH3:24])[O:6][CH2:7][CH2:8][CH:9]=[CH:10][Sn](CCCC)(CCCC)CCCC)([CH3:4])([CH3:3])[CH3:2].OS(C(F)(F)F)(=O)=O.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)#[N:35]>CN(C=O)C.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>[C:1]([Si:5]([CH3:24])([CH3:25])[O:6][CH2:7][CH2:8][CH:9]=[CH:10][C:45]1[CH:44]=[CH:43][C:42]([C:39]2[CH:38]=[CH:37][C:36]([C:34]#[N:35])=[CH:41][CH:40]=2)=[CH:47][CH:46]=1)([CH3:2])([CH3:3])[CH3:4].[NH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 85142049Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silaneHCID 874412284'-Cyanobiphenyl triflate

Product 2

HCID 222AmmoniaHCID 684069964'-[4-(Tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-biphenyl-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compound
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 31B (4.95 g, 10.4 mmol), 4′-cyanobiphenyl triflate (3.1 g, 9.48 mmol, prepared from 4′-hydroxybiphenyl-4-carbonitrile by standard methods), and Pd(PPh3)2Cl2 (0.332 g, 0.47 mmol) in DMF (20 mL) was stirred at 80° C. overnight. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (97.5:2.5 hexane/ethyl acetate) to provide the title compound, 1H NMR (300 MHz, CDCl3): δ 0.07 (s, 6H), 0.91 (s, 9H), 2.46 (q, J=6 Hz, 2H), 3.75 (t, J=6 Hz, 2H), 6.32 (d, J=16 Hz, 1H), 6.48 (d, J=16 Hz, 1H), 7.44 (d, J=9 Hz, 2H), 7.54 (d, J=9 Hz, 2H), 7.65-7.74 (m, 4H) MS (DCl—NH3) m/z 364 (M+H)+, m/z 359 (M+NH4)+

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (97.5:2.5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a191a8220eb547aaa62ab4057f4607a2
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829041B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes