Tetrahydrofuran → 3-Bromo-7-iodothieno[3,2-c]pyridin-4(5H)-one

HRID 734314ノート

反応式

HRID 734314 の反応式
[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C1C(=O)N([I:19])C(=O)C1.C1COCC1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[C:10]([I:19])[C:5]=2[S:4][CH:3]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 578451273-Bromo-7-iodothieno[3,2-c]pyridin-4(5H)-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The mixture of compound 10 (see Example 4(c)) (1.9 g, 8.3 mmol) and N-iodosuccimide (NIS, 2.2 g, 49.9 mmol) in DMF (25 ml) and THF (20 ml) was stirred for 5 hours at 40° C. The reaction mixture was poured into 10% Na2SO3 and ethyl acetate. The insoluble product was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (990 mg). The filtrate was collected, dried over Na2SO4, filtered and concentrated in vacuo. The generated precipitate was washed with MeOH to further yield 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (1.1 g). 1H NMR (400 MHz, DMSO-d6) ppm 11.75 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H).

後処理

  1. filtrationThe insoluble product was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried under reduced pressure

出典と根拠

ORDレコード
ord-1ca07353cebc4c92b0524f23949653c1
出典データセット
uspto-grants-2009_09
特許番号
US07592352B2

反応ノート

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