Iodine → 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 68919

반응식

HRID 68919 반응식
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5].FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:27])C=CC=1)=O.II.OS([O-])=O.[Na+]>C(Cl)Cl>[I:27][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:4]([N:3]([O:2][CH3:1])[CH3:15])=[O:5]

참가 물질

6

반응물 4

HCID 807IodineHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamideHCID 23665763Sodium Bisulfite

생성물 1

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To the N-methoxy-N-methyl-1H-indazole-3-carboxamide (IX) (20 g, 97.4 mmol) in 1 L DCM was added bis(trifluoroacetoxy)iodobenzene (46 g, 107 mmol) followed by portionwise addition of iodine (14.84 g, 58.5 mmol) at r.t. After 1 hour, 600 mL of saturated NaHSO3 was added and a solid began to precipitate which was filtered and rinsed with excess DCM. The filtrate was washed with brine, dried over MgSO4, concentrated and the remaining solid was triturated with a minimal amount of DCM. The combined solids were dried under vacuum over KOH to produce 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (X) as a white solid (23.2 g, 70 mmol, 72% yield). 1H NMR (DMSO-d6) δ ppm 3.45 (s, 4H), 3.77 (s, 4H), 7.45-7.54 (m, 1H), 7.66 (dd, J=8.81, 1.51 Hz, 1H), 8.40 (d, J=1.01 Hz, 1H); ESIMS found for C10H10IN3O2 m/z 331 (M+H).

후처리

  1. customto precipitate which
  2. filtrationwas filtered
  3. washrinsed with excess DCM
  4. washThe filtrate was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customthe remaining solid was triturated with a minimal amount of DCM
  8. dry with materialThe combined solids were dried under vacuum over KOH

출처 및 근거

ORD 기록
ord-8661c5eb07474683b1435d57239cbbd1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822478B2

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