Methanesulfonic Acid → HCID 66766901, 화합물

HRID 1661989노트

반응식

HRID 1661989 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:7][N:6]=[CH:5]2.CS(O)(=O)=O.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl.C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:7]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)[N:6]=[CH:5]2

참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 66766802Ethyl 5-hydroxy-1H-indazole-6-carboxylate

생성물 1

HCID 66766901HCID 66766901, 화합물수율 77.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 5-hydroxy-1H-indazole-6-carboxylate (15.5 g, 75 mmol) in DCM (100 mL) and THF (100 mL) containing methanesulfonic acid (721 mg, 7.5 mmol) is added a solution of 3,4-dihydro-2H-pyran (6.6 g, 79 mmol) in DCM (20 mL) dropwise at RT. The resulting solution is stirred at RT overnight. After the solvent is removed, EtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added. The organic layer is separated, dried and concentrated. The residue is purified by silica gel column chromatography to afford the product (16.8 g, 77% yield). MS (m/z): 291.1 (M+H).

후처리

  1. customAfter the solvent is removed
  2. additionEtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added
  3. customThe organic layer is separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8937b823eadf447196f9616fe66a247d
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030302B2

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