Chlorotrimethylsilane → HCID 58808722, compound

HRID 1921316Notes

Reaction equation

HRID 1921316 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12]2[C:13]([CH3:22])=[N:14][C:15]([O:20]C)=[C:16]([CH2:18][CH3:19])[CH:17]=2)[CH:9]=[CH:8][CH:7]=1)=[O:5])C.C[Si](Cl)(C)C>C(#N)C>[CH2:18]([C:16]1[C:15](=[O:20])[NH:14][C:13]([CH3:22])=[C:12]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[N:11]=2)[CH:17]=1)[CH3:19]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 67492516HCID 67492516, compound

Product 1

HCID 58808722HCID 58808722, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

5′-Ethyl-6′-methoxy-2′-methyl-[2,3′]bipyridinyl-6-carboxylic acid ethyl ester (750 mg, 2.5 mmol) is suspended in acetonitrile and, after addition of KI (1.04 g, 6.25 mmol) and trimethylsilyl chloride, heated to 80° C. under argon for 3 h. This is followed by cooling to room temperature, concentration, addition of 50 ml of water and filtration with suction. The resulting ester (710 mg) is dissolved in MeOH/THF (4/1, 10 ml) and stirred with 1N LiOH solution (7.5 ml) at RT. After 1.5 h, 2N KHSO4 solution is used to acidify, and the precipitate is filtered off with suction. The mother liquor is concentrated and dried in vacuo overnight. The precipitate and the residue are combined and purified by chromatography on silica gel with ethyl acetate/methanol (1/1); yield: 630 mg (98%). MS: m/e=259 (M+H). 1H-NMR (D6-DMSO, δ ppm) 11.65 (s, 1H); 7.91 (t, 1H, J=7.7 Hz); 7.84 (d, 1H, J=7.7 Hz); 7.60 (d, 1H, J=7.7 Hz); 7.51 (s, 1H); 2.42 (q, 2H, J=7.4 Hz); 2.33 (s, 3H); 1.11 (t, 3H, J=7.4 Hz).

Workup

  1. temperatureby cooling to room temperature
  2. concentrationconcentration, addition of 50 ml of water and filtration with suction
  3. dissolutionThe resulting ester (710 mg) is dissolved in MeOH/THF (4/1, 10 ml)
  4. filtrationthe precipitate is filtered off with suction
  5. concentrationThe mother liquor is concentrated
  6. customdried in vacuo overnight
  7. custompurified by chromatography on silica gel with ethyl acetate/methanol (1/1)

Sources & evidence

ORD record
ord-a092f7501eeb4a21b80e68ede84ab644
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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