Potassium Phosphate, Tribasic → [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester

HRID 1784842노트

반응식

HRID 1784842 반응식
[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:8]=[C:7](Br)[CH:6]=1.CC1(C)C(C)(C)OB([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:6]=[C:7]([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:39]([CH3:40])[CH3:41])[CH:8]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:10]=1

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 50994354[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

생성물 1

HCID 50994359[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester수율 70.6%

시약·촉매·용매 2

HCID 178482708HCID 178482708, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester (316 mg, 0.94 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.377 mg, 0.94 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (53 mg, 0.094 mmol) were dissolved in dioxane (6 mL) under nitrogen. Aqueous 2M K3PO4 (1 mL, 1.2 mmol) was added and the mixture was heated at reflux overnight. The reaction mixture was filtered through Celite® and the solvent was removed. The product was chromatographed to give 0.350 g (70% yield) of [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite®
  4. customthe solvent was removed
  5. customThe product was chromatographed

출처 및 근거

ORD 기록
ord-44a512c93d614393a6546052294ee94c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504401B2

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