Cesium carbonate → HCID 86681327, compound

HRID 1778920Notes

Reaction equation

HRID 1778920 reaction equation
[O:1]1[C:3]2([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.[CH3:10][C:11]1[NH:15][C:14]([C:16]#[N:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[OH:1][C:3]1([CH2:2][N:15]2[C:11]([CH3:10])=[CH:12][CH:13]=[C:14]2[C:16]#[N:17])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5706055-Methyl-1H-pyrrole-2-carbonitrileHCID 6429411-oxaspiro[2.6]nonane

Product 1

HCID 86681327HCID 86681327, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Oxaspiro[2,6]nonane (2.5 g), 5-methyl-1H-pyrrole-2-carbonitrile (2.1 g) and Cs2CO3 (6.45 g) in N,N-dimethylformamide (15 mL) was heated at 120° C. in a Biotage Initiator microwave reactor for 30 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and concentrated. The residue was purified by reverse phase chromatography, and was eluted with 30%-70% acetonitrile in 0.1% TFA water solution to provide the title compound.

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customThe residue was purified by reverse phase chromatography
  4. washwas eluted with 30%-70% acetonitrile in 0.1% TFA water solution

Sources & evidence

ORD record
ord-c56891ea55ca4501999b575e23ef7b9a
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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