2-Methylpyridine → HCID 10063380, compound

HRID 2213094Notes

Reaction equation

HRID 2213094 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=O.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]>CC(C)=O.C(Cl)Cl.O>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([C:3]2[CH:25]=[C:20]3[N:19]([CH:2]=2)[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 2

HCID 79752-MethylpyridineHCID 219565182-Bromo-1-[3-methoxy-4-(pyridin-2-yl)phenyl]ethan-1-one

Product 1

HCID 10063380HCID 10063380, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (0.44 mmol) and 2-picoline (41 mg, 0.44 mmol) in acetone (2 mL) was heated to reflux for 3 h, diluted with CH2Cl2 (20 mL) and water (10 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×10 mL), and the combined organic layers were dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:19 to 1:2) to afford 2-(3-methoxy-4-pyridin-2-ylphenyl)indolizine. 1H NMR (CDCl3, 300 MHz) δ 8.75 (m, 1H), 7.92 (m, 2H), 7.86 (d, 1H), 7.73 (dt, 1H), 7.65 (br s, 1H), 7.41 (dd, 1H), 7.38 (d, 1H), 7.30 (br s, 1H), 7.21 (m, 1H), 6.77 (s, 1H), 6.69 (dd, 1H), 6.49 (dt, 1H), 3.97 (s, 3H) ppm. 13C NMR (CDCl3, 75 MHz) δ 157.3, 156.0, 149.4, 137.3, 135.7, 133.7, 131.5, 129.1, 127.2, 125.1, 125.1, 121.6, 119.1, 119.1, 117.6, 110.8, 109.6, 109.2, 96.8, 55.7 ppm. MS (ESI) 301 (M)+.

Workup

  1. temperatureto reflux for 3 h
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2 (2×10 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:19 to 1:2)

Sources & evidence

ORD record
ord-df2fdbbb57a94b31b637419f95a7e722
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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