Phthalimide → HCID 57894445, compound

HRID 1677831Notes

Reaction equation

HRID 1677831 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18](O)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([N:46]1[C:42](=[O:52])[C:43]2[C:44](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:45]1=[O:47])[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57894441HCID 57894441, compound

Product 1

HCID 57894445HCID 57894445, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-ol (0.6 mmol), Ph3P, (1 mmol), phthalimide (1.8 mmol) in 5 mL of dry THF at 0° C., was added DIAD (1 mmol) drop wise. The mixture was warmed up to room temperature gradually and stirred overnight. The solution was poured into water, and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (10% EtOAc:hexane) to yield 170 mg of title compound.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with H2O (×3), brine (×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe material was purified by flash chromatography (10% EtOAc:hexane)

Sources & evidence

ORD record
ord-a029fab9f68b45c1864a535b10fc352e
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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