Sodium Carbonate → 3-[2-chloro-6-(2,3-dimethylphenyl)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 2088990

반응식

HRID 2088990 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[CH3:27][C:28]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.C(OCC)(=O)C>[Cl:26][C:4]1[CH:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:7]=[C:2]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([CH3:34])[C:28]=2[CH3:27])[N:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 866498693-(2,6-dichloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 871915433-[2-chloro-6-(2,3-dimethylphenyl)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridine수율 13.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 86587095Dimethoxyethane ethanol water용매

실험 절차

To a solution of Example 7a (0.08 g, 0.2 mmol), in 2 mL dimethoxyethane/ethanol/water (7:2:3) was added 2,3-dimethylphenylboronic acid (0.036 g, 0.27 mmol), catalytic dichlorobis(triphenylphosphine) palladium(II) and 0.297 mL of 1M aqueous sodium carbonate. The contents were heated at 150 degrees for 30 minutes in a microwave. The reaction was diluted with ethyl acetate and washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (gradient elution, ethyl acetate/hexane 0-50%). The material obtained (35 mg) after concentration of the fractions was purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm), eluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A) to give 9 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 2.19-2.27 (m, 3H) 2.33 (s, 3H) 6.94-7.53 (m, 4H) 7.80 (d, J=9.52 Hz, 2H) 8.19-8.55 (m, 3H) 12.36 (s, 1H). MS (ESI+) m/z 333.9 (M+H)+.

후처리

  1. temperatureThe contents were heated at 150 degrees for 30 minutes in a microwave
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using flash chromatography (gradient elution, ethyl acetate/hexane 0-50%)
  7. customThe material obtained (35 mg) after concentration of the fractions
  8. customwas purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm)
  9. washeluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A)

출처 및 근거

ORD 기록
ord-c8916297911b4bec9b0a5b640ae7f68a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435980B2

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