tert-Butanol → Trifluoroacetic acid

HRID 1521600노트

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HRID 1521600 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.[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]

참가 물질

8

반응물 4

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

생성물 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

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 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-f14590fb1c4a4e0899a717956ae759aa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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