Hydrochloric Acid → 6-Iodo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 2068335

반응식

HRID 2068335 반응식
C[O:2][C:3]([C:5]1[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7][N:8]2[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:9]=12)=[O:4].CO.O1CCCC1.Cl>[Li+].[OH-].O.C(OC(=O)C)C>[I:14][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([N:7]=[C:6]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:5]=2[C:3]([OH:4])=[O:2])[CH:13]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 887Methanol2회HCID 8028TetrahydrofuranHCID 59233743Methyl 6-iodo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate

생성물 1

HCID 592337716-Iodo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid수율 85%

시약·촉매·용매 3

HCID 962Water용매HCID 3939Lithium Hydroxide용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

Methyl-6-iodo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate (250 mg, 0.661 mmol) was dissolve in aqueous LiOH (2N, 1 mL), methanol (2 mL) and tetrahydrofuran (7 mL). This solution was stirred overnight at 45° C. After 24 hours, 2 mL 2M LiOH and 2 mL methanol were added. Heated at 55° C. overnight. The reaction was cooled on an ice water bath and aqueous hydrochloric acid (10 mL, 1N) was added dropwise until acidic by pH paper. Ethylacetate (200 mL) and water (40 mL) were added. The organic portion was extracted with brine (20 mL) and was dried over magnesium sulfate. The solvent was removed by rotory evaporation. The residue was place under vacuum overnight to give of a white solid (204 mg, 85%). 1H NMR (500 MHz, DMSO-D6) δ ppm 7.47 (m, 3H) 7.77 (m, 2H) 7.97 (d, J=9.46 Hz, 1H) 9.27 (s, 1H).

후처리

  1. waitAfter 24 hours
  2. temperatureHeated at 55° C. overnight
  3. temperatureThe reaction was cooled on an ice water bath
  4. extractionThe organic portion was extracted with brine (20 mL)
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed by rotory evaporation
  7. customunder vacuum overnight

출처 및 근거

ORD 기록
ord-630eca440c32488da2f8aceb6c15c856
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293909B2

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