Cesium carbonate → 5-(4-Methoxypiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336404노트

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HRID 336404 반응식
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH3:12][O:13][CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 776664-MethoxypiperidineHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

생성물 1

HCID 591863525-(4-Methoxypiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine수율 693%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 6228Dimethylformamide용매

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온도
180 °C

실험 절차

A suspension of 5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine (69.2 mg, 0.325 mmol, 1 equiv), 4-methoxypiperidine (150 mg, 1.3 mmol, 4.0 equiv), cesium carbonate (212 mg, 0.652 mmol, 2.00 equiv), XPhos (16.9 mg, 0.0354 mmol, 0.109 equiv), and tris(dibenzylideneacetone)dipalladium (0) (9.3 mg, 0.010 mmol, 0.031 equiv) in N,N-dimethylformamide (2 mL) was heated to 180° C. in the microwave for 15 min. The reaction mixture was concentrated in vacuo. The resulting residue was partitioned between ethyl acetate (5 mL) and saturated aqueous sodium chloride solution (5 mL). The aqueous was extracted with ethyl acetate (2×5 mL). The combine organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromotagraphy (95:5 dichloromethane/methanol) afforded a white solid (557 mg, 67%). LCMS (ESI) m/z: 248.3. NMR (500 MHz, CDCl3), δ: 7.32 (m, 1H), 7.05 (m, 1H), 6.23 (m, 1H), 4.39 (br s, 2H), 3.66 (m, 2H), 3.48 (m, 1H), 3.41 (s, 3H), 3.18 (m, 2H), 2.08 (m, 2H), 1.89 (m, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe resulting residue was partitioned between ethyl acetate (5 mL) and saturated aqueous sodium chloride solution (5 mL)
  3. extractionThe aqueous was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combine organic was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromotagraphy (95:5 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-f35e097a1ff5487da5b8e60e39d33109
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889673B2

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