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Ethanol → tert-butyl N-[4-[3-(2-amino-6-methyl-4-nitrophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216204
ノート
印刷プレビュー

反応式

HRID 2216204 の反応式
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([C:10]1[S:11][C:12]([S:27][CH3:28])=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].Br[C:31]1[C:36]([CH3:37])=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[CH:33][C:32]=1[NH2:41].C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([C:10]1[S:11][C:12]([S:27][CH3:28])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:31]3[C:32]([NH2:41])=[CH:33][C:34]([N+:38]([O-:40])=[O:39])=[CH:35][C:36]=3[CH3:37])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 218862412-Bromo-3-methyl-5-nitroanilineHCID 140043492[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]boronic acid

生成物 1

HCID 145857628tert-butyl N-[4-[3-(2-amino-6-methyl-4-nitrophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate
収率 33%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A flask with a stirbar was charged with {[4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 140: step a (752 mg, 1.65 mmol), 2-bromo-3-methyl-5-nitro-phenylamine ((Example 295: step g) 306 mg, 1.32 mmol), aqueous Na2CO3 (2M, 4 mL, 8 mmol), ethanol (4 mL) and toluene (8 mL). The solution was sparged with argon for 10 min and Pd(PPh3)4 (294 mg, 0.25 mmol) was added. The biphasic solution was vigorously stirred under inert atmosphere at 80° C. for 16 h, then was cooled to rt. EtOAc (40 mL) and water (20 mL) were added and the layers were separated. The organic layer was washed with saturated NaHCO3 (2×20 mL), brine (20 mL) and was dried over sodium sulfate. Removal of the solvents in vacuo followed by column chromatography (10–40% EtOAc in hexanes) of the residue yielded the title compound (245 mg, 33%) as a yellow solid. 1H-NMR (CDCl3): δ 8.03 (ddd, 1H, J=1.2, 2.1, 8.1 Hz), 7.91 (s, 1H), 7.90 (t, 1H, J=1.6 Hz), 7.69 (t, 1H, J=7.9 Hz), 7.53 (app dd, 1H, J=0.7, 2.3 Hz), 7.50 (dt, 1H, J=1.4, 7.7 Hz), 7.44 (app dd, 1H, J=0.5, 2.3 Hz), 3.70 (s, 2H), 2.59 (s, 3H), 2.00 (s, 3H), 1.51 (s, 9H).

後処理

  1. customThe solution was sparged with argon for 10 min
  2. temperaturewas cooled to rt
  3. customthe layers were separated
  4. washThe organic layer was washed with saturated NaHCO3 (2×20 mL), brine (20 mL)
  5. dry with materialwas dried over sodium sulfate
  6. customRemoval of the solvents in vacuo

出典と根拠

ORDレコード
ord-9f6ac26b2f2b4fa0a1e138e61fb2b0b4
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109354B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート