Tributylstannane → HCID 86635682, compound

HRID 2427765Notes

Reaction equation

HRID 2427765 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][CH3:14])=[C:7]2[C:3]=1[CH2:4][N:5]([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[CH3:17])[C:6]2=O.C([SnH](CCCC)CCCC)CCC.[F-].[K+]>C1C=CC=CC=1>[CH3:12][O:11][C:10]1[CH:2]=[C:3]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=1)[CH2:6][N:5]([CH:16]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[CH3:17])[CH2:4]2

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 522689Potassium FluorideHCID 66873357HCID 66873357, compound

Product 1

HCID 86635682HCID 86635682, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-bromo-5,7-Dimethoxy-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1 one (0.112 g, 0.27 mmol) in benzene under N2 atmosphere was added 2,2′-azobis(2-methyl propionitrile) AIBN (5.0 mg), followed by tributyl tin hydride (0.145 mL, 0.55 mmol). The resulting mixture was refluxed in an oil bath for 2 h. The reaction was monitored by GC-MS for the disappearance of starting material. The reaction mixture was cooled to room temperature and stirred with potassium fluoride (200 mg) for 45 min. The solids were filtered and the filtrate was concentrated. The resulting material was purified using column chromatography (typically 40% ethyl acetate in hexanes) to give 5,7-Dimethoxy-2-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-lone (0.056 g, 63%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.43 (d, 3H), 3.63 (s, 3H), 3.68 (d, 1H), 3.74 (s, 3H), 3.99 (d, 1H), 5.53 (q, 1H), 6.23 (dd, 2H), 7.15 (m, 4H). GC-MS: m/z 331 (M)+, 316 (M−15)+.

Workup

  1. temperatureThe resulting mixture was refluxed in an oil bath for 2 h
  2. filtrationThe solids were filtered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting material was purified

Sources & evidence

ORD record
ord-08c12e04698d4190981454150ff96d5c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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