Potassium Carbonate → HCID 67250154, compound

HRID 2427735Notes

Reaction equation

HRID 2427735 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C[O:15][C:16](=O)[C:17]1[C:22]([I:23])=[C:21]([F:24])[CH:20]=[CH:19][C:18]=1[CH2:25]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:24][C:21]1[C:22]([I:23])=[C:17]2[C:18]([CH2:25][N:9]([CH2:8][C:7]3[CH:10]=[CH:11][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:5][CH:6]=3)[C:16]2=[O:15])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 67250389HCID 67250389, compound

Product 1

HCID 67250154HCID 67250154, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-trifluoromethoxy-benzyl amine (0.763 mL, 5.0 mmol), 2-bromomethyl-5-fluoro-6-iodo-benzoic acid methyl ester (1.49 g, 4.0 mmol), and K2CO3 (0.828 g, 1 mmol) in toluene (7 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-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.717 g, 40%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.18 (s, 2H), 4.79 (s, 2H), 7.14-7.38 (m, 6H). GC-MS: m/z 451 (M)+, 366 (M−85)+.

Workup

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

Sources & evidence

ORD record
ord-78b0933c6d024610be80dfa08f710311
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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