2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate

HRID 595111ノート

反応式

HRID 595111 の反応式
[NH2:1][C:2]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:6]2[O:7][CH2:8][CH:9]3[CH:13]=[CH:12][CH2:11][N:10]3[C:5]2=[CH:4][CH:3]=1.[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.N1C=CC=CC=1>[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:1][C:2]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:6]2[O:7][CH2:8][C:9]3[N:10]([CH:11]=[CH:12][CH:13]=3)[C:5]2=[CH:4][CH:3]=1)(=[O:29])=[O:28]

参加物

5

反応物 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86712820Methyl 7-amino-3a,4-dihydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate2 回

生成物 1

HCID 70983589methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate収率 14.8%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 7-amino-3a,4-dihydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate (Intermediate 17, 0.370 g) was suspended in a mixture of DCM (6 mL) and pyridine (2.43 mL) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.493 g) was added. The resultant deep red solution was stirred at room temperature overnight then concentrated in vacuo. The residue was diluted with DCM and water and passed through a phase separator. The organic layer was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-30% to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-4H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate (0.107 g) as a white solid.

後処理

  1. additionwas added
  2. concentrationthen concentrated in vacuo
  3. additionThe residue was diluted with DCM and water
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-30%

出典と根拠

ORDレコード
ord-b149553c172a4e3684a3369b97c95f14
出典データセット
uspto-grants-2016_01
特許番号
US09242997B2

反応ノート

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