Iodine → HCID 178490703, 화합물

HRID 76257

반응식

HRID 76257 반응식
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]

참가 물질

6

반응물 4

HCID 807IodineHCID 2734658(Bromomethyl)cyclobutaneHCID 5462224MagnesiumHCID 178490700HCID 178490700, 화합물

생성물 1

HCID 178490703HCID 178490703, 화합물수율 53.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-dcb3816657c6423bb7d60e30145bf6c9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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