Potassium Carbonate → HCID 67250083, compound

HRID 2427731Notes

Reaction equation

HRID 2427731 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH2:12])[CH3:11])=[CH:6][CH:5]=1.C[O:16][C:17](=O)[C:18]1[C:23]([I:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=1[CH2:26]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:25][C:21]1[CH:20]=[C:19]2[C:18](=[C:23]([I:24])[CH:22]=1)[C:17](=[O:16])[N:12]([CH:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)[CH3:11])[CH2:26]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14883544(2-[4-(Trifluoromethoxy)phenyl]ethyl)amineHCID 67252371HCID 67252371, compound

Product 1

HCID 67250083HCID 67250083, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-trifluoromethoxy-phenyl)-ethylamine (0.246 mL, 1.2 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.372 g, 1.0 mmol), and K2CO3 (0.276 g, 2 mmol) in toluene (3 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 5-Fluoro-7-iodo-2-[1-(4-trifluoromethoxy-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.192 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.68 (d, 3H), 3.88-4.26 (dd, 2H), 5.78 (q, 1H), 7.06 (d, 1H), 7.20 (d, 2H), 7.41 (d, 2H), 7.67 (d, 1H). GC-MS: m/z 465 (M)+, 450 (M−15)+.

Workup

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

Sources & evidence

ORD record
ord-b9bc76648cf34f3cb8ce48a9b4b0131b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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