Phthalimide → CPPHA

HRID 1786773Notes

Reaction equation

HRID 1786773 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH2:21]Br)=[O:12])(=O)C.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])=[C:15]([CH2:21][N:27]2[C:23](=[O:33])[C:24]3[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:26]2=[O:28])[CH:16]=1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 57598294HCID 57598294, compound

Product 1

HCID 9931205CPPHAYield 47.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Compound 1-3 (6.0 g 0.015 moles) was dissolved in 50 mL of DMF. To that pthalimide (3.31 g 0.023 moles), K2CO3 (6.2 g 0.045 moles) and a catalytic amount of KI were added and allowed to stir at 50° C. overnight. Upon completion the reaction was diluted with ethyl acetate and then washed with brine (6×25 mL's) to afford 2.9 grams of 1-4 in a crude mixture, which was then purified by normal phase chromatography. 1H NMR (300 MHz, CDCl3): 4.83 ppm (2H, S); 7.05 ppm (2H, m); 7.36 ppm (1H, dd, J=2.4 Hz, 8.6 Hz); 7.50 ppm (1H, dt, J=1.5 Hz, 8.5 Hz); 7.59 ppm (1H, d, J=2.4 Hz); 7.75 ppm (3H, m); 7.91 ppm (2H, m); 8.18 ppm (1H, d, 7.2 Hz); 10.17 ppm (1H, s); 12.27 ppm (1H,s) Analytical LCMS: single peak (214 nm) at 3.633 min (CH3CN/H2O/1% TFA, 4 min gradient), HRMS calc'd for C22H15N2O4Cl (M+H), 407.0799; found 407.0793 (M+H).

Workup

  1. washwashed with brine (6×25 mL's)

Sources & evidence

ORD record
ord-a2c913bf9bf347f6b586e138b6521831
Source dataset
uspto-grants-2009_03
Patent number
US07507836B2

Reaction notes

Loading…