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

HRID 968552노트

반응식

HRID 968552 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9dfefa3017db41628b0a02164e22d89d
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304061B2

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