Pyridine → Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate

HRID 605374ノート

反応式

HRID 605374 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37](Cl)=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([S:8][C:9]4[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][C:10]=4[N+:19]([O-:21])=[O:20])=[CH:6][CH:7]=3)=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 343679-Fluorenylmethyl chloroformateHCID 67040833Ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate

生成物 1

HCID 67040709Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A suspension of the product of Example 430B (0.500 g, 1.541 mmol) and 9-fluorenylmethoxycarbonyl chloride (0.478 g, 1.849 mmol) in methylene chloride (10 mL) under a nitrogen atmosphere was treated with pyridine (0.25 mL, 3.083 mmol), and the resulting solution stirred for 18 hours at room temperature. The reaction was diluted with methylene chloride (50 mL) and washed with 1N aqueous HCl (50 mL) then water (50 mL). The organic was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. Purification by silica gel flash chromatography eluting with methylene chloride afforded the title compound as a bright yellow solid (0.842 g, quantitative). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.23 (t, J=7.17 Hz, 3 H) 4.24 (q, J=7.23 Hz, 2 H) 4.35 (t, J=6.43 Hz, 1 H) 4.57 (d, J=6.25 Hz, 2 H) 7.29-7.50 (m, 4 H) 7.69 (s, 4 H) 7.77 (d, J=7.35 Hz, 2 H) 7.92 (d, J=7.35 Hz, 2 H) 8.11 (s, 1 H) 10.15 (s, 1 H); MS (ESI+) m/z 564 (M+NH4)+, 569 (M+Na)+.

後処理

  1. washwashed with 1N aqueous HCl (50 mL)
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customPurification by silica gel flash chromatography
  6. washeluting with methylene chloride

出典と根拠

ORDレコード
ord-373641299b014b3ba492f834d8658aeb
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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