Water → Methyl 4-methyl-2-(2-(4-(pyridin-4-yl)phenyl)acetamido)thiophene-3-carboxylate

HRID 2098164Notes

Reaction equation

HRID 2098164 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH3:21])[C:16]=2[C:17]([O:19][CH3:20])=[O:18])=[O:10])=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][C:15]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([C:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)=[CH:3][CH:4]=2)[S:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 68755598Methyl 2-(2-(4-iodophenyl)acetamido)-4-methylthiophene-3-carboxylate

Product 1

HCID 45104966Methyl 4-methyl-2-(2-(4-(pyridin-4-yl)phenyl)acetamido)thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 2-(2-(4-iodophenyl)acetamido)-4-methylthiophene-3-carboxylate (420.4 mg, 1.01 mmol), 4-pyridylboronic acid (Aldrich, 167 mg, 1.36 mmol), tetrakis(triphenylphosphine)palladium(0) (123 mg, 0.11 mmol), and potassium carbonate (565 mg, 4.1 mmol) were combined in DME (2 mL) and water (1 mL) in a sealed tube, and heated to 80° C. over 17 h. The reaction mixture was cooled to rt, then partitioned between EtOAc and water. The organic layer was separated, washed (brine), dried (Na2SO4), filtered and concentrated under reduced pressure. Flash chromatography (EtOAc/hexanes) afforded the titled compound. 1H NMR (CDCl3) δ11.3 (s, 1H), 8.67 (dd, J=4.7, 1.4H, 2H), 7.67 (d, J=8.2 Hz, 2H), 7.60-7.40 (m, 4H), 6.38 (s, 1H), 3.88 (s, 2H), 3.80 (s, 3H), 2.33 (s, 3H); 13C NMR (CDCl3) δ167.7, 166.6, 150.3, 149.9, 147.8, 137.4, 134.8, 134.6, 130.3, 127.7, 121.5, 113.0, 112.3, 51.5, 43.5, 17.8; MH+ 367.1.

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed (brine)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c809f54b42684f0d836bd2a6c9831805
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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