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

HRID 1783247

反応式

HRID 1783247 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
22.5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1bcdcc36dd6d44ec80d1dda3af44d1d1
出典データセット
uspto-grants-2009_03
特許番号
US07498436B2

関連ノート

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