Sodium Carbonate → HCID 89462671, compound

HRID 1525319Notes

Reaction equation

HRID 1525319 reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 89462193HCID 89462193, compound

Product 1

HCID 89462671HCID 89462671, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N-(2-(6-iodopyridin-3-yl)propan-2-yl)acetamide, 33-d, (22 g, 72.4 mmol) in dioxane (100 ml) was added 4-bromophenylboronic acid (16 g, 79.6 mmol) and Pd(PPh3)4 (4.2 g, 3.62 mmol) and aq Na2CO3 (2N) (25.3 g, 238.8 mmol). The reaction mixture was then stirred at 95° C. for 3 hours. The reaction mixture was then cooled to room temperature and concentrated under vacuo. The concentrate was extracted with ethyl acetate, washed with brine, and re-concentrated. Purification by silica gel (petroleum ether:ethyl acetate=1:1-ethyl acetate) gave the solid, 33-e, (18 g, 75%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated under vacuo
  3. extractionThe concentrate was extracted with ethyl acetate
  4. washwashed with brine
  5. concentrationre-concentrated
  6. customPurification by silica gel (petroleum ether:ethyl acetate=1:1-ethyl acetate)

Sources & evidence

ORD record
ord-ed13ec90a0834f849dd59f914f1e1b65
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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