Sodium Methoxide → HCID 15603085, compound

HRID 1784854Notes

Reaction equation

HRID 1784854 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:11]=[C:12]([NH:35][C:36](=[O:38])[CH3:37])[CH:13]=[C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][N:20]4[Si](C(C)C)(C(C)C)C(C)C)[CH:15]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.[CH3:39][O-:40].[Na+]>CO>[NH:20]1[C:21]2[C:17](=[C:16]([C:14]3[CH:13]=[C:12]([NH:35][C:36](=[O:38])[CH3:37])[CH:11]=[C:10]([C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([O:40][CH3:39])[CH:7]=4)=[O:9])[CH:15]=3)[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86609397HCID 86609397, compound

Product 1

HCID 15603085HCID 15603085, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-[3-(2-Chloro-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide (Example 83, 0.120 g, 0.22 mmol) in 25 mL of anhydrous methanol was added 0.036 g (0.66 mmol) NaOMe. The reaction mixture was refluxed overnight. The methanol was removed under vacuum and water added to the reaction mixture. The aqueous phase was extracted with ethyl acetate, washed with water and brine and dried over anhydrous sodium sulfate. The crude product was purifed on the preparative SFC to give 10 mg N-[3-(1H-indol-4-yl)-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-acetamide. 1H NMR (400 MHz, CD3COCD3): δ 10.46 (s, 1H), 9.50 (s, 1H), 8.41 (q, J=1.7 Hz, 1H), 8.37 (dd, J=5.1, 0.7 Hz, 1H), 8.11 (q, J=1.5 Hz, 1H), 7.82 (t, J=1.6 Hz, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.45-7.42 (m, 1H), 7.28 (dd, J=5.1, 1.4 Hz, 1H), 7.20 (m, 2H), 7.08 (t, J=1.1 Hz, 1H), 6.75-6.73 (m, 1H), 3.96 (s, 3H), 2.14 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe methanol was removed under vacuum and water
  3. additionadded to the reaction mixture
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-55753a3062bd498994465846621d4331
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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