Tributylstannane → HCID 16039718, compound

HRID 252076Notes

Reaction equation

HRID 252076 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]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[C:6]2=[O:15].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)[C:6](=[O:15])[N:5]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:21][CH:22]=1)[CH2:4]2

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 522689Potassium FluorideHCID 67315692HCID 67315692, compound

Product 1

HCID 16039718HCID 16039718, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-bromo-5,7-Dimethoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1 one (0.200 g, 0.45 mmol) in benzene under N2 atmosphere was added 2,2′-azobis(2-methyl proponitrile) AIBN (5.0 mg), followed by tributyl tin hydride (0.238 mL, 0.9 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-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1one (0.106 g, 64%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.82 (s, 3H), 3.95 (s, 3H), 4.17 (s, 2H), 4.72 (s, 2H), 6.43 (d, 2H), 7.16 (d, 2H), 7.32 (d, 2H). GC-MS: m/z 367 (M)+, 349 (M-18)+.

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-d4cb0cfc0b4f4330a334849be6ce5d08
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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