Sodium Carbonate → 3-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-phenylpyridine

HRID 365910

反応式

HRID 365910 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].C(=O)([O-])[O-].[Na+].[Na+].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>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>[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:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 229618073-(1-Boc-2-(r)-azetidinylmethoxy)-5-bromo-6-chloropyridine

生成物 1

HCID 229618093-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-phenylpyridine収率 78.5%

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
90 °C

実験手順

To a mixture of 3-(1-BOC-2-(R)-azetidinylmethoxy)-5-bromo-6-chloropyridine (0.25 g, 0.68 mmol), tetrakis(triphenylphosphine)palladium(0) (25 mg, 1%), aqueous sodium carbonate (2.0 M, 1 mL) in toluene (10 mL), was added phenylboronic acid (0.108 g, 0.89 mmol). The reaction mixture was stirred and heated at 90° C. for 16 h. Solvent was evaporated. The residue was chromatographed (silica gel; hexane/EtOAC, 10:1 to 2:1) to afford an oil (0.20 g, 78%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 4H), 1.58 (s, 5H), 2.24-2.40 (m, 2H), 3.89 (t, 2H, J=7.5 Hz), 4.15 (dd, 1H, J=3.0, 10.0 Hz), 4.36 (m, 1H), 4.52 (m, 1H), 7.27 (d, 1H, J=3.0 Hz), 7.45 (s, 5H), 8.12 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 347 (M+H)+.

後処理

  1. customSolvent was evaporated
  2. customThe residue was chromatographed (silica gel; hexane/EtOAC, 10:1 to 2:1)

出典と根拠

ORDレコード
ord-036c62610ec9449f9f8193aa58ec6a81
出典データセット
uspto-grants-2000_10
特許番号
US06127386

関連ノート

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