Potassium Carbonate → HCID 57839146, compound

HRID 733073Notes

Reaction equation

HRID 733073 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si](C(C)C)(C(C)C)C(C)C)[CH:9]=[CH:10][C:3]=12.[C:21]([O-])([O-])=O.[K+].[K+].Cl.[CH2:28]([O:30][C:31](=[O:35])[CH2:32][NH:33][CH3:34])[CH3:29]>CN(C=O)C>[CH2:28]([O:30][C:31]([C:32]1[N:33]([CH3:34])[C:2]2[C:7]([CH:21]=1)=[CH:6][N:5]=[C:4]1[C:3]=2[CH:10]=[CH:9][NH:8]1)=[O:35])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57839146HCID 57839146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (700 mg, 2.08 mmol) is dissolved in DMF. After the addition of K2CO3 (573 mg, 4.16 mmol) followed by sarcosine ethyl ester hydrochloride (383.3 mg, 2.49 mmol) the reaction mixture is stirred at 65° C. for 36 hours. The reaction mixture is then cooled down and poured onto ice cold water. The residue is collected by filtration and is dried to give the crude product which is then purified by silica gel column chromatography to yield the desired compound: 1H NMR 400 MHz (DMSO-d6) δ 12.41 (s, 1H), 8.68 (s, 1H), 8.57 (s, 1H), 7.75 (d, 1H, J=3.0 Hz), 6.73 (d, 1H, J=3.1 Hz), 4.32 (q, 2H, J=6.8 Hz), 4.28 (s, 3H), 1.35 (t, 3H, J=6.8 Hz); MS m/z 244.1 (M+1).

Workup

  1. temperatureThe reaction mixture is then cooled down
  2. additionpoured onto ice cold water
  3. filtrationThe residue is collected by filtration
  4. customis dried
  5. customto give the crude product which
  6. customis then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9601f7bcac814a188e5d67a6af703fd9
Source dataset
uspto-grants-2009_09
Patent number
US07589101B2

Reaction notes

Loading…