Triphenylphosphine → HCID 22490022, compound

HRID 2180137Notes

Reaction equation

HRID 2180137 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.[Br:38][CH2:39][CH2:40][CH2:41]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:38][CH2:39][CH2:40][CH2:41][O:36][C:30]1[CH:29]=[C:28]2[C:33]([C:24]([O:23][C:22]3[C:14]([F:13])=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([CH3:37])=[CH:16]4)=[CH:25][N:26]=[N:27]2)=[CH:32][C:31]=1[O:34][CH3:35]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline

Product 1

HCID 22490022HCID 22490022, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DEAD (0.47 ml, 2.95 mmol) was added dropwise to a solution of 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (0.5 g, 1.47 mmol), (prepared as described in Example 4), 3-bromopropan-1-ol (0.2 ml, 2.21 mmol) and triphenylphosphine (0.78 g, 2.95 mmol) in DMF (10 ml). The mixture was stirred for 1 hour at ambient temperature and the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/methylene chloride (1/1). The fractions containing the expected product were combined and evaporated to give 7-(3-bromopropoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline (0.6 g, 88%) (purity 80%; contaminated by some triphenylphosphine oxide).

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe residue was purified by column chromatography
  3. washeluting with ethyl acetate/methylene chloride (1/1)
  4. additionThe fractions containing the expected product
  5. customevaporated

Sources & evidence

ORD record
ord-d7ab508818cb4c928f6860061cf41285
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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