Toluene → HCID 11195507, compound

HRID 1777422Notes

Reaction equation

HRID 1777422 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[N:13][CH:14]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>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.C(O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[N:13][CH:14]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 11195507HCID 11195507, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of toluene and ethanol (9 mL, 2:1) of 1-(5-bromopyridin-2-yl)ethanone (200 mg, 1 mmol) was added (4-methoxyphenyl) boronic acid (304 mg, 2 mmol), 2M Na2CO3 (2.84 mL), and Pd(PPh3)4 (11 mg, 0.01 mmol) under argon atmosphere and heating was continued for 5 hours at 70° C. The reaction mixture was concentrated under vacuum and diluted with water (100 mL) and extracted with EtOAc (2×200 mL). The combined extracts were washed with brine solution (20 mL), and organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. This, on purification by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane eluent, afforded 1-(5-(4-methoxyphenyl)pyridin-2-yl)ethanone as off-white solid (200 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.99 (d, 1H), 8.20 (dd, 1H), 7.97 (d, 1H), 7.76 (d, 2H), 7.07 (d, 2H), 3.81 (s, 3H), 2.63 (s, 3H); LC-MS m/z calculated for [M+H]+ 228.27. found 228.4.

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additiondiluted with water (100 mL)
  4. extractionextracted with EtOAc (2×200 mL)
  5. washThe combined extracts were washed with brine solution (20 mL), and organic layer
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customto obtain crude product
  9. customThis, on purification by flash chromatography (silica gel, 60-120μ)

Sources & evidence

ORD record
ord-a5eee6576cbf467995676f3ab0081959
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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