Triethylamine → 3-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-(trimethylsilylethynyl)pyridine

HRID 2305198ノート

反応式

HRID 2305198 の反応式
[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:21])=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>C1(C)C=CC=CC=1.[I+].[Cu+].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>[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:21])=[C:18]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 229618073-(1-Boc-2-(r)-azetidinylmethoxy)-5-bromo-6-chloropyridine

生成物 1

HCID 229618103-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-(trimethylsilylethynyl)pyridine収率 62.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 178505377HCID 178505377、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-(1-BOC-2-(R)-azetidinylmethoxy)-6-chloro-5-bromopyridine (660 mg, 1.75 mmol) in toluene (20 mL) was added NEt3 (0.7 mL), copper (I) iodine (33 mg), tetrakis(triphenylphosphine)palladium (0) (201 mg) and (trimethylsilyl)acetylene (0.30 mL, 2.10 mmol). The reaction mixture was stirred and heated at 100° C. for 16 h. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtoAc, 5:1 to 2:1) to afford an oil (430 mg, 62%): 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.20-2.40 (m, 2H), 3.80-3.92 (m, 2H), 4.10 (m, 1H), 4.30 (m,1H), 4.50 (m, 1H), 7.37 (d, 1H, J=3.0 Hz), 8.05 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 395 (M+H)+.

後処理

  1. customSolvent was evaporated
  2. customthe residue was chromatographed (silica gel; hexane/EtoAc, 5:1 to 2:1)

出典と根拠

ORDレコード
ord-0f8336b224414bbc84aeb43735409178
出典データセット
uspto-grants-2002_08
特許番号
US06437138B1

反応ノート

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