Tributylvinyltin → 2-(Benzyloxy)-3-nitro-6-vinylpyridine

HRID 2370836ノート

反応式

HRID 2370836 の反応式
[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([Sn](CCCC)(CCCC)CCCC)=[CH2:20]>C1(C)C=CC=CC=1.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>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([CH:19]=[CH2:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 225652672-(Benzyloxy)-6-chloro-3-nitropyridine

生成物 1

HCID 866879862-(Benzyloxy)-3-nitro-6-vinylpyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a stirred mixture of (2-(benzyloxy)-6-chloro-3-nitropyridine (3.2 g, 0.0123 mol) in toluene (32.5 mL) in a 250 mL sealed tube, were added Pd(PPh3)4 (426 mg, 0.000369 mol, Aldrich) and vinyl tributyltin (3.90 g, 0.0123 mol). The tube was purged with the argon gas for 10 min, capped and stirred for 12 h at 110° C. After completion of the reaction (monitored by TLC, 10% EtOAc in hexane), the reaction mixture was quenched with water (20 mL) and extracted with EtOAc (50 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, and purified by column chromatography, silica gel (60-120 mesh) using 5-7% EtOAc in petroleum ether as an eluent to afford the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.47 (d, J=8.1 Hz, 1H), 7.52 (d, J=6.9 Hz, 1H), 7.43-7.27 (m, 3H), 7.20 (br. s., 2H), 6.92-6.83 (m, 1H), 6.49 (dd, J=17.4, 1.5 Hz, 1H), 5.74 (dd, J=10.5, 1.5 Hz, 1H), 5.59 (s, 2H). MS (ESI, positive ion) m/z: 257 (M+H).

後処理

  1. customsealed tube
  2. customThe tube was purged with the argon gas for 10 min
  3. customcapped
  4. customAfter completion of the reaction (monitored by TLC, 10% EtOAc in hexane)
  5. customthe reaction mixture was quenched with water (20 mL)
  6. extractionextracted with EtOAc (50 mL×3)
  7. dry with materialdried over anhydrous sodium sulfate
  8. custompurified by column chromatography, silica gel (60-120 mesh)

出典と根拠

ORDレコード
ord-852f2fa061374db8a45fd4f0f592b427
出典データセット
uspto-grants-2014_04
特許番号
US08710043B2

反応ノート

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