Triphenylphosphine → HCID 9906959, compound

HRID 991015Notes

Reaction equation

HRID 991015 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.O[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[O:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:3]3[C:4]4[CH2:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]=4[NH:1][N:2]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 135512470HCID 135512470, compound

Product 1

HCID 9906959HCID 9906959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol (0.76 g, Example 30) 4-(2-hydroxyethyl)morpholine (0.85 g), triphenylphosphine (1.77 g) and dichloromethane (20 ml) were stirred together with ice/water bath cooling and diethylazodicarboxylate (1.16 g) was added dropwise. The resultant mixture was allowed to warm to room temperature and stirred for about 24 hours. The solvent was evaporated off under reduced pressure and the residue purified by flash column chromatography on silica using ethyl acetate/ethanol (25%) to give a solid. The solid was triturated with diethyl ether (10 ml) and the solid filtered, washed with diether and dried at about 65° C. to give 3-[4-(2-morpholinoethoxy)phenyl]-1,4-dihydroindeno[1,2-c]pyrazole, m.p. 175-6° C.

Workup

  1. temperaturecooling
  2. stirringstirred for about 24 hours
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue purified by flash column chromatography on silica
  5. customto give a solid
  6. customThe solid was triturated with diethyl ether (10 ml)
  7. filtrationthe solid filtered
  8. washwashed with diether
  9. customdried at about 65° C.

Sources & evidence

ORD record
ord-224b351a3bf6493e84174d343b578f94
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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