Trimethylsilyldiazomethane → HCID 86683671, compound

HRID 1509308Notes

Reaction equation

HRID 1509308 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([CH2:30][CH:31]=[CH2:32])=[CH:20][C:21]4[N:26]([CH3:27])[C:25](=[O:28])[CH2:24][O:23][C:22]=4[N:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:34][Si](C=[N+]=[N-])(C)C>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([CH2:30][C:19]2[C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH:7][C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][CH2:10][CH2:11]4)=[CH:17][CH:16]=3)=[N:29][C:22]3[O:23][CH2:24][C:25](=[O:28])[N:26]([CH3:27])[C:21]=3[CH:20]=2)[CH2:34][CH2:32]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 123751593HCID 123751593, compound

Product 1

HCID 86683671HCID 86683671, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml 3 necks round-bottomed flask was tert-butyl(1-(4-(7-allyl-1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (52 mg, 0.116 mmol), palladium acetate (32 mg, 0.180 mmol) in diethyl ether (5 ml) to give a yellow solution at room temperature under a nitrogen atmosphere. The reaction mixture was cooled to 0° C. and trimethylsilyldiazomethane (2 ml) was added via a plastic syringe. The reaction mixture was left stirring at 0° C. for 10 minutes and warmed up to room temperature overnight.

Workup

  1. customto give a yellow solution at room temperature under a nitrogen atmosphere
  2. waitThe reaction mixture was left
  3. temperaturewarmed up to room temperature overnight

Sources & evidence

ORD record
ord-158ce7cf7cbf41dd858c4512b5fb3fd1
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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