Nitrogen → HCID 58424545, compound

HRID 1408834Notes

Reaction equation

HRID 1408834 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]2[C:20](=[CH:21][C:22]=1[CH3:23])[O:19][C:13]1([CH2:18][CH2:17][CH2:16][O:15][CH2:14]1)[CH2:12][C:11]2=[O:24].[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)#[N:26].N#N>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.O.O1CCOCC1>[CH3:23][C:22]1[CH:21]=[C:20]2[C:10]([C:11](=[O:24])[CH2:12][C:13]3([O:19]2)[CH2:18][CH2:17][CH2:16][O:15][CH2:14]3)=[CH:9][C:8]=1[C:31]1[CH:32]=[C:27]([CH:28]=[CH:29][CH:30]=1)[C:25]#[N:26]

Participants

8

Reactant 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 58424460HCID 58424460, compound

Product 1

HCID 58424545HCID 58424545, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 10 mL CEM microwave test tube was charged with Cs2CO3 (147 mg, 0.45 mmol), PdCl2(PPh3)2 (8 mg, 0.011 mmol), 6-bromo-7-methyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (70 mg, 0.225 mmol), 3-cyanophenylboronic acid (43 mg, 0.293 mmol), dioxane (4 mL) and H2O (0.2 mL), the system was swept with N2 and sealed, and heated in a CEM microwave reactor at 100° C. for 10 min. The reaction mixture was filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%) to give 3-(7-methyl-4-oxo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-6-yl)benzonitrile (72 mg). MS ESI+ve m/z 334 (M+H)+.

Workup

  1. customsealed
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%)

Sources & evidence

ORD record
ord-ab064bbfde3446aca7dcfbcea6e13bd9
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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