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Triphenylphosphine → HCID 69314044, compound

HRID 2222268
Notes
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Reaction equation

HRID 2222268 reaction equation
I[C:2]1[CH:6]=[CH:5][N:4]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:37]1([Zn])[CH:42]=[CH:41][CH:40]=[CH:39][NH:38]1>C1COCC1.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>[CH:8]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[N:4]1[CH:5]=[CH:6][C:2]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:3]1)([CH3:10])[CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 142471191H-Pyrrole, 3-iodo-1-[tris(1-methylethyl)silyl]-HCID 178528051HCID 178528051, compound

Product 1

HCID 69314044HCID 69314044, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-iodo-1-(triisopropylsilyl)-1H-pyrrole (11.0 g, 2.87 mmol), triphenylphosphine (27 mg, 0.103 mmol), and tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.069 mmol) in THF (20 mL) was degassed with Ar (g) for 15 min, then 2-bromo(pyridin-2-yl)zinc (1.5 mL of 0.5M solution, 5.74 mmol) was added and degassing continued a further 15 min. The reaction was stirred at 70° C. for 5 h and monitored by LC/MS. The reaction mixture was quenched with H2O (40 mL) then extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:9) to afford 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]pyridine as a clear oil which was used below without further purification.

Workup

  1. customdegassing
  2. customThe reaction mixture was quenched with H2O (40 mL)
  3. extractionthen extracted with EtOAc (3×25 mL)
  4. washthe combined organic extracts washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customthe crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:9)

Sources & evidence

ORD record
ord-78dde0ad53bc47f4989329e7237990f0
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371767B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes