Methyltriphenylphosphonium iodide → HCID 57480688, compound

HRID 1962798Notes

Reaction equation

HRID 1962798 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:28][C:29]1[CH:30]=[C:31]([CH:35]([N:39]2[CH:43]=[C:42]([C:44]3[C:45]4[CH:52]=[CH:51][N:50]([CH2:53][O:54][CH2:55][CH2:56][Si:57]([CH3:60])([CH3:59])[CH3:58])[C:46]=4[N:47]=[CH:48][N:49]=3)[CH:41]=[N:40]2)[CH2:36][CH:37]=O)[CH:32]=[CH:33][CH:34]=1>C1COCC1>[Br:28][C:29]1[CH:30]=[C:31]([CH:35]([N:39]2[CH:43]=[C:42]([C:44]3[C:45]4[CH:52]=[CH:51][N:50]([CH2:53][O:54][CH2:55][CH2:56][Si:57]([CH3:60])([CH3:58])[CH3:59])[C:46]=4[N:47]=[CH:48][N:49]=3)[CH:41]=[N:40]2)[CH2:36][CH:37]=[CH2:1])[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 574780023-(3-bromophenyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal

Product 1

HCID 57480688HCID 57480688, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Potassium tert-butoxide in THF (1M, 200 μL) was added to a solution of methyltriphenylphosphonium iodide (80 mg, 0.0002 mol) in THF (2 mL, 0.02 mol) at 0° C. The reaction was stirred at room temperature for 1 h and then cooled to −78° C. The 3-(3-bromophenyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal (90 mg, 0.0002 mol) in THF (2 mL, 0.02 mol) was added dropwise. The reaction was allowed to warm to room temperature gradually. The reaction was partitioned between water and EtOAc. The organic layer was washed with saturated NaCl, dried over MgSO4, filtered and concentrated to give an oil. The product was purified by FCC on silica gel eluting with EtOAc:Hexane, (1:1) to give 4-{1-[1-(3-bromophenyl)but-3-en-1-yl]-1H-pyrazol-4-yl}-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (35 mg, 40%) as an oil. m/z=524, 526 (M+1).

Workup

  1. temperaturecooled to −78° C
  2. temperatureto warm to room temperature gradually
  3. customThe reaction was partitioned between water and EtOAc
  4. washThe organic layer was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe product was purified by FCC on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-472d58370261489b820f31ca8567b2de
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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