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

HRID 1521596ノート

反応式

HRID 1521596 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dead50725b4a412a97fac6976be2a670
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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