Sodium Carbonate → Methyl 4'-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl)[1,1'-biphenyl]-3-carboxylate

HRID 14034

반응식

HRID 14034 반응식
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:2][CH3:3].[CH3:29][N:30]([S:32]([C:35]1[CH:40]=[CH:39][C:38](Br)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:29][N:30]([CH3:31])[S:32]([C:35]1[CH:36]=[CH:37][C:38]([C:15]2[CH:16]=[C:7]([C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:26][CH2:27][CH3:28])=[O:6])[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=2)=[CH:39][CH:40]=1)(=[O:33])=[O:34]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 21086174Methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 69680482Methyl 4'-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl)[1,1'-biphenyl]-3-carboxylate

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
22.5 °C

실험 절차

A mixture of methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step 1, 534 mg, 1.4 mmol), 4-bromobenzenedimethyl-sulfonamide (363 mg, 1.4 mmol), and sodium carbonate (2 mL of a 2 M mixture in water, 4.1 mmol) in toluene (10 mL) is degassed under reduced pressure for 15 minutes and then purged with argon. Palladium tetrakis(triphenylphosphine) (40 mg, 0.025 mmol) is added and the reaction mixture is degassed under reduced pressure for 15 minutes and then purged with argon. The reaction mixture is heated at reflux for 4 hours, cooled to 20-25 degrees C., filtered through a plug of diatomaceous earth and sodium sulfate, and the filtrate is concentrated under reduced pressure. Purification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1) gives methyl 4′-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylate (XXXVIII), ESI-MS (m/z) [M+H]+=447.

후처리

  1. customis degassed under reduced pressure for 15 minutes
  2. custompurged with argon
  3. customthe reaction mixture is degassed under reduced pressure for 15 minutes
  4. custompurged with argon
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for 4 hours
  7. filtration, filtered through a plug of diatomaceous earth and sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customPurification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1)

출처 및 근거

ORD 기록
ord-42392731874643368907e936cf482ccc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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