Tetramethyltin → HCID 86649469, compound

HRID 2190922Notes

Reaction equation

HRID 2190922 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:21])[O:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)=[O:8])[CH3:2].[CH3:23][Sn](C)(C)C>CN(C)C=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:21])[O:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([CH3:23])[CH:13]=2)=[O:8])[CH3:2]

Participants

6

Reactant 2

HCID 11661TetramethyltinHCID 86649468HCID 86649468, compound

Product 1

HCID 86649469HCID 86649469, compoundYield 61.7%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [(7-bromo-4-hydroxy-2-oxo-2H-chromene-3-carbonyl)-amino]-acetic acid ethyl ester (212 mg, 0.563 mmol), tetramethyltin (0.158 mL, 1.14 mmol) and Pd(PPh3)2Cl2 (20 mg, 0.029 mmol) in N,N-dimethylformamide (2 mL) was heated in a 120° C.-oil bath under nitrogen for 1 h; then cooled, diluted with ethyl acetate, washed with water, saturated NaCl solution, and ethyl acetate phase was dried over Na2SO4, filtered, concentrated and column purified to give desired product (106 mg). ESI (m/z): 306 (M+H)+.

Workup

  1. temperaturethen cooled
  2. washwashed with water, saturated NaCl solution, and ethyl acetate phase
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customcolumn purified

Sources & evidence

ORD record
ord-8ade800a31fa4693afd2e64bd5bddd52
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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