Potassium Phosphate, Tribasic → [2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

HRID 626680ノート

反応式

HRID 626680 の反応式
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[C:19](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH2:20].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:22]([O:21][C:19](=[O:26])[NH:20][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1)([CH3:25])([CH3:24])[CH3:23]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970444-Bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 69671929[2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester収率 74%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-bromo-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (166 mg, 0.51 mmol), tert-butyl carbamate (297 mg, 2.54 mmol), Pd2(dba)3 (23 mg, 0.025 mmol), Xantphos (29 mg, 0.05 mmol) and potassium phosphate tribasic (216 mg, 1.02 mmol) in toluene (5 mL) and water (1 mL) was degassed with argon then heated at 60° C. for 1.5 hours. The reaction mixture was cooled to room temperature and then filtered through Celite® washing with ethyl acetate. The filtrate was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-35% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (137 mg, 74% yield). LCMS (Method C): RT=2.30 min, m/z: 348 [M−C4H7+].

後処理

  1. customwas degassed with argon
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite®
  4. washwashing with ethyl acetate
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by silica gel flash chromatography (0-35% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-19ab2b9e799c44e69d55adf4582d5844
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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