Ethyl pyridine-4-acetate → HCID 12051089, compound

HRID 412080Notes

Reaction equation

HRID 412080 reaction equation
[N+:1]([C:3](S(C1C=CC(C)=CC=1)(=O)=O)=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)#[C-:2].[N:23]1[CH:28]=[CH:27][C:26]([CH2:29]C(OCC)=O)=[CH:25][CH:24]=1.CC(C)([O-])C.[K+]>COCCOC>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:4]2[C:29]([C:26]3[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=3)=[CH:2][NH:1][CH:3]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 736321Ethyl pyridine-4-acetateHCID 23665647Potassium tert-butoxideHCID 54511263HCID 54511263, compound

Product 1

HCID 12051089HCID 12051089, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

1-[(1-isocyano-2-(3-methoxyphenyl)ethenyl)sulfonyl]-4-methylbenzene (9.0 g, 0.0285 mol) was dissolved in dry DME (200 mL) and added dropwise to a cooled (0° C.) mixture of ethyl 4-pyridylacetate (9.0 g, 0.545 mol) and potassium t-butoxide (7.1 g, 0.0633 mol) in dry DME (100 mL). After the addition was complete the reaction was warmed to 25° C. and stirred for 3 h. The reaction was then poured into ice water (1200 mL) and extracted into CH2Cl2 (3×500 mL). The combined organics were dried over Na2SO4, filtered and evaporated in vacuo to give a solid. This solid was then triturated with ether and filtered to give 3.0 g of pure 3-(3-methoxyphenyl)-4-(4-pyridyl)pyrrole. The filtrate was again evaporated in vacuo and then triturated with a 50/50 mixture of CH2Cl2 and ether to give an additional 1.5 g of pure product. Finally the filtrate was evaporated in vacuo and purified on SiO2 eluting with ethyl acetate to give another 0.5 g of pure product resulting in a 70% combined yield. 1HNMR (DMSO-d6) δ 11.38 (1H, br s, NH), 8.37 (2H, d, J=6.1), 7.24-7.17 (4H, m), 7.02-7.00 (1H, m), 6.80-6.77 (3H, m), 3.68 (3H, s).

Workup

  1. additionadded dropwise to
  2. temperaturea cooled
  3. additionAfter the addition
  4. extractionextracted into CH2Cl2 (3×500 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a solid
  9. customThis solid was then triturated with ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-d40756b0faa4462ba9654a6cf726b05b
Source dataset
uspto-grants-2003_05
Patent number
US06562843B1

Reaction notes

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