Triphenylphosphine → HCID 69918445, compound

HRID 2307825Notes

Reaction equation

HRID 2307825 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:9][O:10][C:11](=[O:24])[CH:12](O)[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:9][O:10][C:11](=[O:24])[CH:12]([O:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 582762Methyl indole-3-lactateHCID 5995293-Bromo-5-hydroxypyridineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 69918445HCID 69918445, compoundYield 94.6%

Conditions

Temperature
0 °C

Procedure

A 100 mL RBF was charged with 3-bromo-5-hydroxypyridine (1.67 g, 9.58 mmol), 2-hydroxy-3-(1H-indol-3-yl)-propionic acid methyl ester (2.1 g, 9.58 mmol) which was synthesized according to literature method (M. E. Jung et al J. Org. Chem. 1999, 64, 2976) and Ph3P (3.01 g, 11.5 mmol), and was purged with nitrogen. THF (40 mL) was added at 0° C. After stirring at 0° C. for 10 min, DEAD (1.81 mL, 11.5 mmol) was added via syringe. The reaction mixture was stirred at 0° C. for 1 h and at rt overnight. The reaction mixture was concentrated and the residue was separated by flash chromatography (20-60% EtOAc in hexane) to provide the desired product (3.4 g, 94%). MS (DCI) m/z 375, 377 (M+1)+.

Workup

  1. customwas synthesized
  2. customwas purged with nitrogen
  3. additionTHF (40 mL) was added at 0° C
  4. stirringThe reaction mixture was stirred at 0° C. for 1 h and at rt overnight
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was separated by flash chromatography (20-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-624edc284d104f7b842d41d7291e91d9
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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