Sodium hydride → [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine

HRID 985486ノート

反応式

HRID 985486 の反応式
[H-].[Na+].[CH:3]([Si:6]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[SH:7])([CH3:5])[CH3:4].[H][H].I[C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1>C1COCC1.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>[CH3:12][CH:11]([Si:6]([CH:3]([CH3:5])[CH3:4])([S:7][C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1)[CH:8]([CH3:10])[CH3:9])[CH3:13]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 22507076HCID 22507076、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 22507077[6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine収率 95%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (128 mg, 5.1 mmol) in THF (30 ml) was added triisopropylsilanethiol (1.1 ml, 5.1 mmol) dropwise. After the evolution of hydrogen ceased, a solution of {6-[2-(3-Iodophenoxy)ethyl](2-pyridyl) }methylamine (1.2 g, 3.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (390 mg, 0.3 mmol) in toluene (30 ml) was added. After refluxing for 16 h under argon, the reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was dissolved in ethyl acetate and washed with 1N NaOH and brine. The organic layer was dried with sodium sulfate, filtered, and evaporated. The crude product was chomatrographed over silica gel to yield 1.34 g (95%) of [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine. NMR 1H Cl3CD δ: 7.38 (dd, 1H, J=7.2, 8.0 Hz), 7.04 (m, 3H), 6.77 (m, 1H), 6.52 (d, 1H, J=8.0 Hz), 6.25 (d, 1H, J=4.0 Hz), 4.29 (t, 2H, J=6.8 Hz), 3.06 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8Hz), 1.85 (m, 3H), 1.09 (m, 2H).

後処理

  1. temperatureAfter refluxing for 16 h under argon
  2. customevaporated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-67852ab832a540cea70b7882f6b9f223
出典データセット
uspto-grants-2005_03
特許番号
US06872730B2

反応ノート

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