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

HRID 219341

反応式

HRID 219341 の反応式
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

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 887Methanol2 回HCID 8028TetrahydrofuranHCID 59233743Methyl 6-iodo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3939Lithium Hydroxide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

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 rotary 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).

後処理

  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 rotary evaporation
  7. customunder vacuum overnight

出典と根拠

ORDレコード
ord-6283ed272d5b42baaa808a49503ccec4
出典データセット
uspto-grants-2012_06
特許番号
US08198449B2

関連ノート

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