Potassium Carbonate → HCID 59565441, compound

HRID 1962865Notes

Reaction equation

HRID 1962865 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][CH:26]([S:37][CH3:38])[C:27]([NH:29][C:30]([CH2:34][O:35][CH3:36])([CH3:33])[CH:31]=O)=[O:28])=[CH:20][C:19]=2[CH3:39])#[CH:14].C([O-])([O-])=O.[K+].[K+]>CO.C(OCC)(=O)C>[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][CH:26]([S:37][CH3:38])[C:27]([NH:29][C:30]([CH2:34][O:35][CH3:36])([CH3:33])[C:31]#[CH:1])=[O:28])=[CH:20][C:19]=2[CH3:39])#[CH:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59565403HCID 59565403, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 59565441HCID 59565441, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (Bestmann's reagent) (77 mg) and 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide (110 mg) in MeOH (10 ml) was cooled to 0° C. Solid K2CO3 (71 mg) was added and the mixture stirred during 16 hour allowing the temperature raising to 25° C. The reaction mixture was diluted with ethyl acetate and poured onto brine. The water phase was extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate, filtered and evaporated. The crude residue was purified by column chromatography to give 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-prop-2-ynyl)-2-methylsulfanyl-acetamide (60 mg) as a light brown solid as a mixture of diastereoisomers.

Workup

  1. temperatureraising to 25° C
  2. additionpoured onto brine
  3. extractionThe water phase was extracted twice with ethyl acetate
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-d5d66f7745cf48a785dce1f1b502ea5d
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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