tert-Butanol → Trifluoroacetic acid

HRID 1521600ノート

反応式

HRID 1521600 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.[CH3:15][C:16]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[N:28][CH:29]=1)([CH3:23])[CH2:17][O:18][C:19]([F:22])([F:21])[F:20].[C:33](=O)([O-:35])[O-:34].[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>[F:22][C:19]([F:20])([F:21])[C:33]([OH:35])=[O:34].[CH3:23][C:16]([C:24]1[CH:25]=[C:26]([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:27]=[N:28][CH:29]=1)([CH3:15])[CH2:17][O:18][C:19]([F:20])([F:21])[F:22]

参加物

8

反応物 4

HCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 21543699HCID 21543699、化合物HCID 709812375-(2-Methyl-1-(trifluoromethoxy)propan-2-yl)pyridin-3-ylboronic acid

生成物 2

HCID 6422Trifluoroacetic acidHCID 665767717-{5-[2-Methyl-1-(trifluoromethoxy)-2-propanyl]-3-pyridinyl}-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 (50 mg, 0.200 mmol), the title compound from Example 64 Step C (63.1 mg, 0.240 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (28.3 mg, 0.040 mmol) and potassium carbonate (83 mg, 0.600 mmol) were added tert-butanol (2.2 mL) and water (0.28 mL). The vial was capped tightly and heated to 80° C. overnight. The reaction 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) to provide the title compound: LCMS m/z 389.00 [M+H]+; NMR (500 MHz, CD3OD) δ 9.99 (s, 1H), 9.19 (s, 1H), 9.02 (s, 1H), 8.94 (s, 1H), 8.09-8.00 (m, 3H), 4.33 (s, 2H), 3.48-3.45 (m, 2H), 3.39-3.36 (m, 2H), 1.60 (s, 6H).

後処理

  1. customThe vial was capped tightly
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue was diluted with acetonitrile
  5. custompurified by HPLC (C18 column, 10 to 100% acetonitrile/water

出典と根拠

ORDレコード
ord-f14590fb1c4a4e0899a717956ae759aa
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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