Sodium Carbonate → 1-[3-(2-Ethoxy-3,5-diisopropyl-phenyl)-thieno[2,3-c]pyridin-5-yl]-ethanone

HRID 1394637Notes

Reaction equation

HRID 1394637 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:7]([CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=1B(O)O)[CH3:2].Br[C:20]1[C:28]2[C:23](=[CH:24][N:25]=[C:26]([C:29](=[O:31])[CH3:30])[CH:27]=2)[S:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.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>[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:7]([CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=1[C:20]1[C:28]2[C:23](=[CH:24][N:25]=[C:26]([C:29](=[O:31])[CH3:30])[CH:27]=2)[S:22][CH:21]=1)[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 179527371-(3-Bromo-thieno[2,3-c]pyridin-5-yl)-ethanoneHCID 18504242(2-Ethoxy-3,5-diisopropylphenyl)-boronic acid

Product 1

HCID 596820741-[3-(2-Ethoxy-3,5-diisopropyl-phenyl)-thieno[2,3-c]pyridin-5-yl]-ethanoneYield 91.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

2-Ethoxy-3,5-diisopropyl-phenyl-boronic acid (586 mg, 2.34 mmol) was dissolved in toluene (10 ml). 1-(3-Bromo-thieno[2,3-c]pyridin-5-yl)-ethanone (310 mg, 1.21 mmol), and tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.12 mmol) followed by 2M sodium carbonate solution (2.34 ml) was added to this solution. This mixture was then heated to 90° C. overnight, then poured into brine (20 ml) and extracted with ethyl acetate (2×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The residue was then purified by chromatography (chromatotron, 4μ plate, 10% ethyl acetate in hexanes) to give a 1-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-thieno[2,3-c]pyridin-5-yl]-ethanone as a white solid (422.2 mg, 91%). 1H NMR (250 MHz, CDCl3): δ 9.14 (s, 1H), 8.38 (s, 1H), 7.80 (s, 1H), 7.13 (d, 1H, J=1.9), 6.98 (d, 1H, J=1.9), 3.33 (m, 1H), 3.28 (q, 2H, J=7.5), 2.87 (m, 1H), 2.74 (s, 3H), 1.25 (s, 3H), 1.23 (s, 3H), 1.22 (s, 3H), 1.20 (s, 3H), 0.85 (t, 3H, J=7.5). MS [EI+] 382 (M+H)+.

Workup

  1. additionwas added to this solution
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by chromatography (chromatotron, 4μ plate, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-779ddee85f73464fbc788776fbee42ab
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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