Phenol → HCID 59371547, compound

HRID 2095374Notes

Reaction equation

HRID 2095374 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[O:19][N:18]=[C:17]([CH2:20][CH2:21][CH2:22][OH:23])[CH:16]=2)[CH:12]=[N:13][CH:14]=1.[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([C:15]2[O:19][N:18]=[C:17]([CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:16]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59371440HCID 59371440, compound

Product 1

HCID 59371547HCID 59371547, compoundYield 154%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[5-[5-[(1-methyl-2(S)-pyrrolidinyl)methoxy]-3-pyridyl]-3-isoxazolyl]-1-propanol (10 mg, 33 μmol), phenol (5 mg, 50 μmol, 1.5 equiv.) and PPh3 (13 mg, 50 μmol, 1.5 equiv.) in anhydrous THF (0.2 mL) was added diethyl azodicarboxylate (DEAD; 8 μL, 50 μmol, 1.5 equiv.) at 0° C. The mixture was stirred for 1 h at 0° C. and then warmed to room temperature. Stirring was continued for 11 h, then the mixture was concentrated in vacuo. The residue was purified by CC on SiO2 with CH2Cl2/MeOH 9:1 to give 3-[(1-methyl-2(S)-pyrrolidinyl)methoxy]-5-[3-(3-phenoxypropyl)-5-isoxazolyl]pyridine (20 mg, 51%).

Workup

  1. temperaturewarmed to room temperature
  2. stirringStirring
  3. waitwas continued for 11 h
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue was purified by CC on SiO2 with CH2Cl2/MeOH 9:1

Sources & evidence

ORD record
ord-3b52f82880764cffbba24bdb14a75ca6
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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