Triphenylphosphine → 4-(4-Fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(4-pyridyloxy)ethoxy)cinnoline

HRID 2180135Notes

Reaction equation

HRID 2180135 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[C:22]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([OH:36])=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[N:26][CH:25]=2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:37])[NH:18]2.O[CH2:39][CH2:40][O:41][C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[F:13][C:14]1[C:22]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([O:36][CH2:39][CH2:40][O:41][C:42]4[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=4)=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[N:26][CH:25]=2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:37])[NH:18]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 33760122-(Pyridin-4-yloxy)ethanolHCID 5462977Diethyl azodicarboxylateHCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline

Product 1

HCID 224900244-(4-Fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(4-pyridyloxy)ethoxy)cinnolineYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DEAD (0.19 ml, 1.2 mmol) was added dropwise to a solution of 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (0.2 g, 0.6 mmol), (prepared as described in Example 4), 4-(2-hydroxyethoxy)pyridine (0.125 g, 0.9 mmol), (J. Chem. Soc. Perkin II, 1987, 1867), and triphenylphosphine (0.31 g, 1.2 mmol) in DMF (4 ml). After stirring for 2 hours at ambient temperature, the volatiles were removed under vacuum to give an oil that crystallised on standing. The solid was triturated with methylene chloride, filtered, washed with methylene chloride and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(4-pyridyloxy)ethoxy)cinnoline (90 mg, 33%).

Workup

  1. customthe volatiles were removed under vacuum
  2. customto give an oil that
  3. customcrystallised
  4. customThe solid was triturated with methylene chloride
  5. filtrationfiltered
  6. washwashed with methylene chloride
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6a731634a2c44cbb85f63909601b8976
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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