Potassium Carbonate → HCID 67250296, compound

HRID 2427736Notes

Reaction equation

HRID 2427736 reaction equation
Cl.[C:2]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)#[N:3].C[O:13][C:14](=O)[C:15]1[C:20]([I:21])=[C:19]([F:22])[CH:18]=[CH:17][C:16]=1[CH2:23]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:22][C:19]1[C:20]([I:21])=[C:15]2[C:16]([CH2:23][N:3]([CH2:2][C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=3)[C:14]2=[O:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99422504-(Aminomethyl)benzonitrile hydrochlorideHCID 67250389HCID 67250389, compound

Product 1

HCID 67250296HCID 67250296, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-cyano-benzyl amine hydrochloride (0.218 g, 5.0 mmol), 2-bromomethyl-5-fluoro-6-iodo-benzoic acid methyl ester (0.373 g, 1.0 mmol), and K2CO3 (0.276 g, 2 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. The resulting mixture was filtered and concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 6-fluoro-7-iodo-2-(4-cyano-benzyl)-2,3-dihydro-isoindol-1-one (0.100 g, 26%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.84 (s, 2H), 7.22-7.68 (m, 6H). GC-MS: m/z 392 (M)+.

Workup

  1. temperaturewas heated
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2c6d4f49cdbb421a9cf54c8f92af685b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…