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Tris(furan-2-yl)phosphane → 2-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

HRID 9665
Notes
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Reaction equation

HRID 9665 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][C:8]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]34[O:29][CH2:28][C:25]([CH3:30])([CH2:26][O:27]3)[CH2:24][O:23]4)=[C:16]([CH3:31])[CH:15]=2)=[C:9]([CH3:11])[CH:10]=1)CCC.[F:40][C:41]1[CH:48]=[C:47](Br)[CH:46]=[CH:45][C:42]=1[C:43]#[N:44].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCCC1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[F:40][C:41]1[CH:48]=[C:47]([C:6]2[S:7][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]45[O:23][CH2:24][C:25]([CH3:30])([CH2:26][O:27]4)[CH2:28][O:29]5)=[C:16]([CH3:31])[CH:15]=3)=[C:9]([CH3:11])[CH:10]=2)[CH:46]=[CH:45][C:42]=1[C:43]#[N:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 7360294-Bromo-2-fluorobenzonitrileHCID 21986389Tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane2×

Product 1

HCID 219863002-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile

Reagents, catalysts & solvents

2
HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane (intermediate 100, 0.037 g) and 2-fluoro-4-bromobenzonitrile (0.011 g) in tetrahydrofuran (2 ml) was treated with palladium bis(dibenzylideneacetone) (0.0035 g) and trifuranyl phosphine (0.0013 g) and the resulting mixture stirred at reflux for 3 hours. The solvent was removed and the residue purified by Biotage® chromatography using a mixture of petroleum ether:ethyl acetate (4:1) as eluent to give the title compound.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was removed
  3. customthe residue purified by Biotage® chromatography
  4. additiona mixture of petroleum ether:ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-29ab68ec7fbd4c80a56aeb3f91a16063
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091237B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes