Acetonitrile → Methyl 2-[2-(4-methanesulfonylphenyl)thiophen-3-yl]acetate

HRID 2199574Notes

Reaction equation

HRID 2199574 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)(=[O:15])=[O:14].C([O-])([O-])=O.[K+].[K+].CC#N>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.O>[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 57116941Methyl 2-(2-bromothiophen-3-yl)acetate

Product 1

HCID 71230756Methyl 2-[2-(4-methanesulfonylphenyl)thiophen-3-yl]acetate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Intermediate B (2.30 g, 9.78 mmol), 4-methylsulfonylphenylboronic acid (1.96 g, 9.78 mmol), K2CO3 (4.15 g, 30.0 mmol), tetrakis(triphenylphosphine)palladium(0) (150 mg, 0.130 mmol), MeCN (30 ml) and water (10 ml) were heated at 70° C. for 1 hour. The organic phase was removed in vacuo and the crude material was dissolved in DCM. The mixture was purified by flash chromatography using 30% and 50% EtOAc in iso-hexane as eluent. Yield: 2.25 g (74%); white solid. 1H NMR (400 MHz, CDCl3): δ 3.11 (s, 3H), 3.67 (s, 2H), 3.74 (s, 3H), 7.13 (d, J 5.0 Hz, 1H), 7.39 (d, J 5.0 Hz, 1H), 7.67-7.72 (m, 2H), 7.98-8.04 (m, 2H).

Workup

  1. customThe organic phase was removed in vacuo
  2. dissolutionthe crude material was dissolved in DCM
  3. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-252277da2fb340068997b0fe1aaa8bbe
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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