Phthalimide → HCID 67231570, compound

HRID 876391Notes

Reaction equation

HRID 876391 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[Si:13]([O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[N:35]3[CH:36]=[CH:37][C:38]([CH2:40]O)=[CH:39][C:34]3=[N:33][N:32]=1)[CH:27]=[CH:26]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[C:42]1(=[O:52])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[NH:43]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Si:13]([O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[N:35]3[CH:36]=[CH:37][C:38]([CH2:40][N:43]4[C:44](=[O:51])[C:45]5[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=5)[C:42]4=[O:52])=[CH:39][C:34]3=[N:33][N:32]=1)[CH:27]=[CH:26]2)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67231369HCID 67231369, compound

Product 1

HCID 67231570HCID 67231570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.6524 mL, 4.143 mmol) was added to a solution of (3-(8-(tert-butyldimethylsilyloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)methanol (1.123 g, 2.762 mmol), isoindoline-1,3-dione (0.6096 g, 4.143 mmol) and triphenylphosphine (1.087 g, 4.143 mmol) in THF (20 mL) at 0° C. Following addition, the cold bath was removed and the reaction stirred at ambient temperature for 3 hours. The crude reaction was concentrated and the residue was purified by flash column chromatography (eluting with at 1:4 mixture of ethyl acetate/Hexanes) to afford the desired product mixed with triphenylphosphine oxide.

Workup

  1. additionaddition
  2. customthe cold bath was removed
  3. customThe crude reaction
  4. concentrationwas concentrated
  5. customthe residue was purified by flash column chromatography (eluting with at 1:4 mixture of ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-833daa9e4dcf441b91438b476051060f
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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