Iodine → HCID 178506359, 화합물

HRID 246364노트

반응식

HRID 246364 반응식
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2C(O)=O.C(=O)(O)[O-].[Na+].[I-:23].[Na+].II>ClC(Cl)C.O.ClCCl>[I:23][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:17])([F:16])[F:1])[CH:5]=2)[NH:9][N:8]=1

참가 물질

8

반응물 4

HCID 807IodineHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 299215515-(trifluoromethoxy)-1H-indazole-3-carboxylic acid

생성물 1

HCID 178506359HCID 178506359, 화합물수율 67%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 5-(trifluoromethoxy)-1H-indazole-3-carboxylic acid (0.2 g, 813 μmol), and sodium bicarbonate (225 mg, 104 μL, 2.68 mmol) in dichloroethane (2 mL) and water (2.00 mL) were added in one portion sodium iodide (317 mg, 2.11 mmol) and iodine (268 mg, 1.06 mmol) and the mixture heated at 100° C. (oil bath temperature) with vigorous stirring for 45 minutes. After cooling to 25° C. the mixture was diluted with dichloromethane, then washed with 10% Na2S2O3 and saturated NaHCO3. The organics were dried (MgSO4) and concentrated to an off-white solid which was dissolved in dichloromethane, cyclohexane added to promote solid formation, and allowed to stand. The solid was separated by filtration and dried to give 3-iodo-5-(trifluoromethoxy)-1H-indazole (178 mg, 543 μmol, 67%) as white needles. MS (M−H)−=326.8; 1H NMR (CDCl3) δ: 7.51 (d, J=9.1 Hz, 1H), 7.40 (s, 1H), 7.32-7.38 (m, 1H).

후처리

  1. temperatureAfter cooling to 25° C. the mixture
  2. washwashed with 10% Na2S2O3 and saturated NaHCO3
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated to an off-white solid which
  5. dissolutionwas dissolved in dichloromethane
  6. additioncyclohexane added
  7. customThe solid was separated by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-2f76e282eb2749f5b33445bff6d3df8c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

반응 노트

불러오는 중…