2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 6-(2-bromo-4-fluorobenzenesulfonylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate

HRID 715985노트

반응식

HRID 715985 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:18]2[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:17]2=[CH:16][CH:15]=1>N1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:13][C:14]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:18]2[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:17]2=[CH:16][CH:15]=1)(=[O:11])=[O:10]

참가 물질

5

반응물 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86712122methyl 6-amino-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate2회

생성물 1

HCID 70983401methyl 6-(2-bromo-4-fluorobenzenesulfonylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate수율 45.6%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

2-Bromo-4-fluorobenzenesulfonyl chloride (0.410 g) was added to a solution of methyl 6-amino-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (Intermediate 55, 0.290 g) in pyridine (10 mL) and DCM (10 mL) and the resultant mixture was stirred at room temperature for 24 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-15% to give a sandy coloured solid which was triturated with ether and filtered to give methyl 6-(2-bromo-4-fluorobenzenesulfonylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (0.268 g).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of methanol and DCM with a gradient of 0-15%
  9. customto give a sandy coloured solid which
  10. customwas triturated with ether
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-3afb836796c444f7a6ff0d2f6abaec80
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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