HCID 352578, compound → HCID 67423437, compound

HRID 1393017Notes

Reaction equation

HRID 1393017 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH3:7][N:8]1[CH2:29][C:14]23[CH2:15][CH2:16][CH:17]4[CH:26]([CH:13]2[CH2:12][CH2:11][CH:10]3[CH:9]1[CH3:30])[CH2:25][CH:24]=[C:23]1[C:18]4([CH3:28])[CH2:19][CH2:20][C:21](=O)[CH2:22]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1(C)C=CC=CC=1.C1COCC1>[CH:1](=[C:21]1[CH2:22][C:23]2[C:18]([CH3:28])([CH:17]3[CH:26]([CH2:25][CH:24]=2)[CH:13]2[CH2:12][CH2:11][CH:10]4[CH:9]([CH3:30])[N:8]([CH3:7])[CH2:29][C:14]24[CH2:15][CH2:16]3)[CH2:19][CH2:20]1)[CH3:2]

Participants

6

Reactant 2

HCID 352578HCID 352578, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67423437HCID 67423437, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (1.0 M in THF, 0.3 mL, 0.30 mmol) was added dropwise to a stirred solution of ethyl triphenylphosphonium bromide (156 mg, 0.42 mmol) in 2 mL anhydrous toluene. A bright orange suspension resulted and was stirred at room temperature for 5 hours. Compound 130B (25 mg, 0.076 mmol) in 1 mL THF was added to the above suspension and stirred overnight. The reaction was quenched with saturated ammonium chloride and extracted with dichloromethane to give the crude product, which was purified on silica gel column eluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane to give the desired product (12 mg, 46% yield).

Workup

  1. customA bright orange suspension resulted
  2. stirringstirred overnight
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted with dichloromethane
  5. customto give the crude product, which
  6. customwas purified on silica gel column
  7. washeluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-68306972987241ddb4561a8e5698c683
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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