Iodine → HCID 178490703、化合物

HRID 76257ノート

反応式

HRID 76257 の反応式
Br[CH2:2][CH:3]1[CH2:6][CH2:5][CH2:4]1.[Mg].II.[C:10]([N:14]1[CH:18]=[C:17]([CH:19]=[O:20])/[C:16](=[N:21]/[C:22](=[O:32])[C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])/[S:15]1)([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([N:14]1[CH:18]=[C:17]([CH:19]([OH:20])[CH2:2][CH:3]2[CH2:6][CH2:5][CH2:4]2)/[C:16](=[N:21]/[C:22](=[O:32])[C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])/[S:15]1)([CH3:13])([CH3:12])[CH3:11]

参加物

6

反応物 4

HCID 807IodineHCID 2734658(Bromomethyl)cyclobutaneHCID 5462224MagnesiumHCID 178490700HCID 178490700、化合物

生成物 1

HCID 178490703HCID 178490703、化合物収率 53.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To (bromomethyl)cyclobutane (211 mg, 1.42 mmol) in THF (20 mL) was added magnesium (41.3 mg, 1.7 mmol), and initiator iodine (10 mg). The mixture was stirred at rt for 2 hrs, then cooled to −40° C. and added to a solution of Example 21A (100 mg, 0.28 mmol) in THF (20 mL). The mixture was allowed to warm to room temperature, quenched with saturated aqueous NH4Cl, and extracted with EtOAc (2×). The organics were combined, dried (MgSO4), filtered and solvent evaporated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 63 mg (53%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.62-1.78 (m, 2 H) 1.65 (s, 9 H) 1.76-1.94 (m, 2 H) 1.97-2.18 (m, 4 H) 2.47-2.59 (m, 1 H) 3.92 (s, 3 H) 4.88 (dd, J=8.29, 6.14 Hz, 1 H) 6.93 (d, J=8.90 Hz, 1 H) 7.37 (dd, J=8.90, 3.07 Hz, 1 H) 7.95 (s, 1 H) 8.05 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 423 (M+H)+.

後処理

  1. temperaturecooled to −40° C.
  2. temperatureto warm to room temperature
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent evaporated
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-dcb3816657c6423bb7d60e30145bf6c9
出典データセット
uspto-grants-2014_09
特許番号
US08835475B2

反応ノート

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