Sodium methanethiolate → 4-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 2216034ノート

反応式

HRID 2216034 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+]([O-])=O)=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Cl:20])=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH3:24][S-:25].[Na+]>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:25][CH3:24])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Cl:20])=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

参加物

3

反応物 2

HCID 4378561Sodium methanethiolateHCID 210571744-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 210571794-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester収率 21%

実験手順

The procedure as in Example 27, a was followed using 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester (3.5 g, 8.10 mmol, Example 118, step b) and sodium thiomethoxide (560 mg, 8.10 mmol as 1M solution in EtOH). The reaction was allowed to stir for 2.5 hours and was quenched with acetic acid. The resulting mixture was dissolved into EtOAc, and aqueous work up with brine and saturated NaHCO3 resulted in isolation of a mixture. This mixture was purified by SiO2 flash column chromatography (Biotage—40 M, 100% hexanes to 25% EtOAc in hexanes). The product was isolated as a yellow solid (750 mg, 21%). ESI-MS (m/z): Calcd. for C12H10BrClNO4S3: 441.8 (M+H); found: 442.1. 1H-NMR (CD3OD+CDCl3): δ 8.93 (m, 1H), 8.50 (m, 1H), 8.06 (s, 1H), 3.91 (m, 3H), 2.67 (m, 3H).

後処理

  1. customwas quenched with acetic acid
  2. dissolutionThe resulting mixture was dissolved into EtOAc, and aqueous work up with brine and saturated NaHCO3
  3. customresulted in isolation of a mixture
  4. customThis mixture was purified by SiO2 flash column chromatography (Biotage—40 M, 100% hexanes to 25% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-10f150658b0544fa8b15b29350c2b2c6
出典データセット
uspto-grants-2006_09
特許番号
US07109354B2

反応ノート

読み込み中…