Water → 1-t-Butyl 2-ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1,2-dicarboxylate

HRID 909455ノート

反応式

HRID 909455 の反応式
[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.Br[C:34]1[N:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:37]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C>[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([C:34]2[N:38]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[C:37]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:36][CH:35]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139787141-tert-Butyl 2-ethyl 5-bromo-1H-pyrrole-1,2-dicarboxylateHCID 666813752-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 666830251-t-Butyl 2-ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1,2-dicarboxylate収率 87.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

2-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.73 g, 18.9 mmol) synthesized in Example (1e) and 1-t-butyl 2-ethyl 5-bromo-1H-pyrrole-1,2-dicarboxylate (8.37 g, 26.3 mmol) synthesized in Example (17b) were dissolved in a mixed solvent of toluene (180 mL) and ethanol (77 mL), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (770 mg, 0.94 mmol) and an aqueous potassium carbonate solution (2M, 23.7 mL, 47.2 mmol) were added, and stirring was carried out at 100° C. for 1 hour under nitrogen atmosphere. After the reaction solution was cooled to room temperature, water (200 mL) was added, and extraction was carried out with ethyl acetate (400 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%) to afford the desired compound (9.44 g, yield 84%) as a pale yellow oil.

後処理

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%)

出典と根拠

ORDレコード
ord-47255d74e86143b88df5e8e8d27d68c7
出典データセット
uspto-grants-2011_09
特許番号
US08017610B2

反応ノート

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