Triphenylphosphine → HCID 59176341, compound

HRID 1095744Notes

Reaction equation

HRID 1095744 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][N:46]1[CH2:50][CH2:49][CH:48]([CH2:51]O)[CH2:47]1.N(C(OCC)=O)=NC(OCC)=O.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([O:25][CH2:51][CH:48]5[CH2:49][CH2:50][N:46]([CH3:45])[CH2:47]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 295970(1-methylpyrrolidin-3-yl)methanolHCID 516892Sodium BicarbonateHCID 66781369HCID 66781369, compound

Product 1

HCID 59176341HCID 59176341, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (300 mg, 0.90 mmol) in anhydrous THF (15 ml) were added at ambient temperature under a nitrogen atmosphere triphenylphosphine (352 mg, 1.34 mmol), (1-methylpyrrolidin-3-yl) methanol (155 mg, 1.34 mmol) and diethyl azodicarboxylate (0.21 ml, 1.34 mmol). The reaction mixture was stirred at ambient temperature under nitrogen atmosphere overnight. The mixture was treated with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with CH2Cl2 and EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product. The crude product was purified by column chromatography on silica gel (elution with 10% MeOH/CH2Cl2) to afford partially purified product. This material was purified by silica gel chromatography (eluting with 10% 7N NH3/MeOH/CH2Cl2) to provide the title compound (34.2 mg, 9% yield) as a solid. MS ESI (+) m/z 433.2 (M+1) detected.

Workup

  1. extractionextracted with CH2Cl2 and EtOAc
  2. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customThe crude product was purified by column chromatography on silica gel (elution with 10% MeOH/CH2Cl2)
  7. customto afford partially purified product
  8. customThis material was purified by silica gel chromatography (eluting with 10% 7N NH3/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-506b2bf6bf8c4d108651ef253a56acbd
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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