Ammonium Hydroxide → HCID 69084435, compound

HRID 1023421Notes

Reaction equation

HRID 1023421 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:4][N:3]=1.[OH-].[NH4+:18].O1CCOCC1>[Cu-]=O.O>[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH:9]=[CH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:18])[CH:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 312751,4-DioxaneHCID 86673606HCID 86673606, compound

Product 1

HCID 69084435HCID 69084435, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A 2 mL microwave reaction tube is charged with the mixture of E and Z 2-bromo-4-(2-o-tolyl-vinyl)-pyridine (510 mg, 1.9 mmol), Copper (I) oxide (53 mg, 0.37 mmol), Ammonium Hydroxide (28%, 0.5 mL) and 1-4-dioxane (0.5 mL). The reaction mixture is heated at 150° C. for 30 min in a microwave reactor. Then water (5 mL) is added and the mixture is extracted with EtOAc (3×20 mL). The combined organic layers are washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude is purified by silica flash column chromatography eluting with EtOAc in Heptane (gradient from 0% to 100%) to give the desired mixture of products (210 mg).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×20 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude is purified by silica flash column chromatography
  6. washeluting with EtOAc in Heptane (gradient from 0% to 100%)
  7. customto give the desired

Sources & evidence

ORD record
ord-0b74d4e245664608aa534dc7385cf1f1
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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