Sodium Carbonate → 4-(5-Methyl-2-phenylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 968552Notes

Reaction equation

HRID 968552 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1.[CH3:15][O:16][C:17]([C:19]1[N:20]([S:33]([C:36]2[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=2[CH3:44])(=[O:35])=[O:34])[CH:21]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.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>[CH3:15][O:16][C:17]([C:19]1[N:20]([S:33]([C:36]2[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=2[CH3:44])(=[O:34])=[O:35])[CH:21]=[C:22]([C:2]2[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:3]=2)[CH:23]=1)=[O:18]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 590158034-Bromo-5-methyl-2-phenylpyridineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Product 1

HCID 691967634-(5-Methyl-2-phenylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

13 (29 mg, 0.12 mmol, 1.0 equiv.) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (52 mg, 0.12 mmol, 1.0 equiv.) were dissolved in benzene (1.2 mL). After adding aqueous Na2CO3 (0.2 mL), Pd(PPh3)4 (28 mg, 0.024 mol, 0.2 equiv.) was then added and the resulting mixture was refluxed for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2SO4, the solvent was removed under reduced pressure. The crude product 14 was used without further purification (100 mg, HPLC Rt=7.005 minutes, ES+ 475.4, ES− not observed).

Workup

  1. additionwas then added
  2. temperaturethe resulting mixture was refluxed for 16 hours
  3. washwashed with water
  4. dry with materialAfter drying the organic layer over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product 14 was used without further purification (100 mg, HPLC Rt=7.005 minutes, ES+ 475.4, ES− not observed)

Sources & evidence

ORD record
ord-9dfefa3017db41628b0a02164e22d89d
Source dataset
uspto-grants-2007_12
Patent number
US07304061B2

Reaction notes

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