Dibutyltin dichloride → 2-{4-[4-(2,5-Dichloro-phenoxy)-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxalin-1-ylmethyl}-cyclopropanecarboxylic acid ethyl ester

HRID 1966972Notes

Reaction equation

HRID 1966972 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH2:15][CH2:14]1)=[O:12].[CH:28]([CH:30]1[CH2:32][CH:31]1[C:33]([O:35][CH2:36][CH3:37])=[O:34])=O.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>>[CH2:36]([O:35][C:33]([CH:31]1[CH2:32][CH:30]1[CH2:28][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]([C:11]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:2]=2[Cl:1])=[O:12])[CH2:14][CH2:15]1)=[O:34])[CH3:37]

Participants

5

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 53311864[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone

Product 1

HCID 533118662-{4-[4-(2,5-Dichloro-phenoxy)-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxalin-1-ylmethyl}-cyclopropanecarboxylic acid ethyl esterYield 46%

Conditions

Temperature
150 °C

Procedure

To a solution of 0.10 g (0.25 mmol) [4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone (Example 3) were added 0.036 g (0.25 mmol) ethyl 2-formyl-1-cyclopropane-carboxylate (commercially available, CAS RN 20417-61-2), 0.008 g (0.026 mmol) dibutyltin dichloride and 0.06 mL (0.50 mmol) phenylsilane. The resulting solution was heated for 10 min. in a microwave oven at 150° C. The light yellow solution was evaporated and dissolved in acetonitrile containing a few drops of N,N-dimethylformamide. The suspension was filtered using a syringe micro filter and purified on a preparative HPLC system (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to give 60 mg (46%) of the desired compound as a light brown foam. MS (ESI): m/z=526.13 [M+H]+.

Workup

  1. customThe light yellow solution was evaporated
  2. dissolutiondissolved in acetonitrile containing a few drops of N,N-dimethylformamide
  3. filtrationThe suspension was filtered
  4. filtrationmicro filter
  5. custompurified on a preparative HPLC system (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-a23555e21c2c4c4c9bf92e877a4b2f93
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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