tert-Butanol → 7-{5-[2-(Ethylsulfonyl)propan-2-yl]pyridin-3-yl}-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoline

HRID 1521596노트

반응식

HRID 1521596 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[CH2:6][CH2:5]2.[CH2:15]([S:17]([C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1)([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:16].C(=O)([O-])[O-].[K+].[K+].C(O)(C)(C)C>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O>[CH2:15]([S:17]([C:20]([C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]2[CH:12]=[N:13][N:14]=[C:7]2[CH2:6][CH2:5]3)[CH:26]=[N:27][CH:28]=1)([CH3:22])[CH3:21])(=[O:18])=[O:19])[CH3:16]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 21543699HCID 21543699, 화합물HCID 89961589(5-(2-(Ethylsulfonyl)propan-2-yl)pyridin-3-yl)boronic acid

생성물 1

HCID 899618957-{5-[2-(Ethylsulfonyl)propan-2-yl]pyridin-3-yl}-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoline

시약·촉매·용매 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 962Water용매

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온도
80 °C

실험 절차

To a vial containing the title compound from Example 22 Step B (0.020 g, 0.080 mmol), the title compound from Example 62 Step E (0.021 g, 0.080 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.132 mg, 1.599 μmol), and potassium carbonate (0.033 g, 0.240 mmol) were added tert-butanol (0.90 mL) and water (0.10 mL). The vial was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction solution was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with acetonitrile and then purified by HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid). Fractions containing product were combined, aqueous 1 N hydrochloric acid solution was added and the solution concentrated to provide the title compound: LCMS m/z 382.99 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 9.42 (s, 1H), 8.97 (s, 1H), 8.83 (s, 1H), 8.29 (s, 1H), 7.93-7.91 (m, 2H), 7.85-7.83 (m, 1H), 3.18-3.13 (m, 4H), 2.96 (q, J=7.43 Hz, 2H), 1.87 (s, 6H), 1.07 (t, J=7.43, 3H).

후처리

  1. customThe vial was flushed with nitrogen
  2. customsealed tightly
  3. temperatureThe reaction solution was then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting residue was diluted with acetonitrile
  6. custompurified by HPLC (C18 column, 10 to 100% acetonitrile/water
  7. additionFractions containing product
  8. additionaqueous 1 N hydrochloric acid solution was added
  9. concentrationthe solution concentrated

출처 및 근거

ORD 기록
ord-dead50725b4a412a97fac6976be2a670
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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