Acetonitrile → HCID 58487345, 화합물

HRID 1036094노트

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HRID 1036094 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[O:10])[CH:5]=[CH:4][C:3]=1Br.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:27](#[N:29])[CH3:28]>O1CCOCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[O:10])[CH:5]=[CH:4][C:3]=1[C:6]1[N:7]([CH3:2])[N:29]=[C:27]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:28]=1

참가 물질

6

반응물 3

HCID 6342AcetonitrileHCID 62657Potassium Phosphate, TribasicHCID 58487036N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide

생성물 1

HCID 58487345HCID 58487345, 화합물수율 4%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

A mixture of N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) (16 mg, 0.05 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (4 mg, 10% mol) and K3PO4 (11 mg, 0.05 mmol) in 0.5 ml ACN, 0.5 ml dioxane, 0.2 ml H2O was bubbled with argon before heated at 85° C. for 4 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated to dryness. Flash silica gel column purification (0-90% B, A: hexane; B: 50% EA in hexane) furnished 2.2 mg crude desired product as yellow solid which was re-purified on prep HPLC to give 0.8 mg N-[6-amino-5-(1-methyl-3-phenylpyrazol-5-yl)(2-pyridyl)](2-fluorophenyl)carboxamide (69) as off-white solid. (yield: 4%, purity>90%).

후처리

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customFlash silica gel column purification (0-90% B
  7. customB: 50% EA in hexane) furnished 2.2 mg crude desired product as yellow solid which
  8. customwas re-purified on prep HPLC

출처 및 근거

ORD 기록
ord-a60c8cf1b6154e6299389adaaa2e4e22
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546403B2

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