3-Aminophenylboronic acid → 3-(1-trityl-1H-imidazol-4-yl)aniline

HRID 1521730노트

반응식

HRID 1521730 반응식
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[N:13]=[CH:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>C1COCC1>[C:17]([N:15]1[CH:16]=[C:12]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])[N:13]=[CH:14]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 922693-Aminophenylboronic acidHCID 522689Potassium FluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 27732744-Bromo-1-trityl-1H-imidazole

생성물 1

HCID 114751133-(1-trityl-1H-imidazol-4-yl)aniline수율 37.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

(3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-t-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone)dipalladium(0) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60° C. for 16 hrs. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with H2O (3×100 mL), brine (100 mL), dried (Na2SO4) and concentrated. The crude product is purified by flash column chromatography using methanol/CH2Cl2 to afford the title compound (1.1 g, 36%).

후처리

  1. customis bubbled through the mixture for 10 min
  2. customthe reaction mixture is sealed
  3. filtrationThe solid is filtered
  4. additionthe filtrate is diluted with EtOAc (250 mL)
  5. washThe solution is washed with H2O (3×100 mL), brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-f2a96b2760834db0aae5f71672fee9cb
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

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