Sodium Methoxide → HCID 15603180, compound

HRID 1784855Notes

Reaction equation

HRID 1784855 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:11]=[C:12]([NH:35]C(=O)C)[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>[NH2:35][C:12]1[CH:11]=[C:10]([C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:40][CH3:39])[CH:7]=2)=[O:9])[CH:15]=[C:14]([C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH:18]=[CH:19][NH:20]3)[CH:13]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86609397HCID 86609397, compound

Product 1

HCID 15603180HCID 15603180, compoundYield 12.9%

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, 0.150 g, 0.27 mmol) in 25 mL of anhydrous methanol was added 0.022 g (0.41 mmol) NaOMe. The reaction mixture was refluxed overnight. The methanol was removed under vacuum and water was 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 by preparative TLC using 10:1 methylene chloride:methanol to give 12 mg [3-amino-5-(1H-indol-4-yl)-phenyl]-(2-methoxy-pyridin-4-yl)-methanone. 1H NMR (400 MHz, CDCl3): δ 8.23 (s, 1H), 8.22 (s, 1H), 7.38 (t, J=1.5 Hz, 1H), 7.34 (t, J=1.0 Hz, 1H), 7.32 (t, J=0.9 Hz, 1H), 7.21-7.16 (m, 4H), 7.13 (dd, J=5.1, 1.3 Hz, 1H), 7.10-7.07 (m, 2H), 7.00 (s, 1H), 6.62-6.59 (m, 1H), 3.91 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe methanol was removed under vacuum and water
  3. additionwas added 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-9a7b2a0b8e31455a800d0c63702ad7c8
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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