Cesium carbonate → HCID 67174251, compound

HRID 2096546Notes

Reaction equation

HRID 2096546 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:17].[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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:17]=[C:5]1[C:4]2[C:14](=[CH:15][CH:16]=[C:2]([C:24]3[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=3)[C:18]#[N:19])[CH:3]=2)[O:13][C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:6]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 58423954HCID 58423954, compound

Product 1

HCID 67174251HCID 67174251, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-2′,3′,5′,6′-tetrahydrospiro[chroman-2,4′-pyran]-4-one (300 mg, 1 mmol), 3-cyanophenylboronic acid (298 mg, 2 mmol), Cs2CO3 (2 M, 4 mL) and Pd(PPh3)2Cl2 (80 mg) in 1,4-dioxane (10 mL) under Ar was stirred under microwave at 120° C. for 35 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified bypreparative TLC to give 3-(4-oxo-2′,3′,5′,6′-tetrahydrospiro[chroman-2,4′-pyran]-6-yl)benzonitrile (140 mg, 43%). 1H-NMR (CDCl3): 1.81-1.85 (m, 2H), 2.00-2.04 (d, 2H), 2.80 (s, 2H), 3.78-3.87 (m, 4H), 7.14 (d, 1H), 7.52-7.56 (t, 1H), 7.61-7.64 (d, 1H), 7.71-7.74 (d, 1H), 7.78 (d, 1H), 7.80 (s, 1H), 8.07 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the residue, which
  3. customwas purified bypreparative TLC

Sources & evidence

ORD record
ord-27e098edd3e0483eb250dbc21dfa2826
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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