1,3-Isobenzofurandione, 5-fluoro- → HCID 17989337, compound

HRID 1353060Notes

Reaction equation

HRID 1353060 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.C1(N=C=N)CCCCC1.Cl.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:39]2C(=O)C3C(=CC=C(OC4C=CC=CC=4)C=3)C2=O)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[N:39]([C:27]1[CH:28]=[CH:29][C:30]([O:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)=[C:25]([O:24][CH3:23])[CH:26]=1)[C:9]2=[O:10]

Participants

6

Reactant 3

HCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 12048208N-CyclohexylcarbodiimideHCID 17989398HCID 17989398, compound

Product 1

HCID 17989337HCID 17989337, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Fluorophthalic anhydride [Acros] (0.84 g, 5 mmol) was dissolved in dichloromethane (30 ml) and polymer bound N-cyclohexylcarbodiimide [Argonaut Technologies] (1.69 mol. eq./g, 3 g) was added, followed by a solution of 3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine [Example A4] (1.18 g, 5.0 mmol) and a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred for 16 h at ambient temperature. The resin was filtered off over filter-aid, and washed with dichloromethane. The filtrate was evaporated in vacuo and purified by chromatography using a Biotage Flash40M cartridge, eluting with dichloromethane-methanol to give the 5-fluoro-2-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-isoindole-1,3-dione;

Workup

  1. additionwas added
  2. filtrationThe resin was filtered off
  3. filtrationover filter-aid
  4. washwashed with dichloromethane
  5. customThe filtrate was evaporated in vacuo
  6. custompurified by chromatography
  7. washeluting with dichloromethane-methanol

Sources & evidence

ORD record
ord-f809c1b0faba449484e122ad174d785c
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

Loading…