Ethylene Glycol → HCID 178517853, 화합물

HRID 2205646노트

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HRID 2205646 반응식
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](I)=[C:22]([F:27])[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:14]2[CH2:15][CH2:16][CH2:17][C@@:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:6][CH2:7][C@@H:2]([OH:1])[CH2:3][CH2:4]4)[CH2:12][CH2:11]3)[CH2:13]2)=[C:22]([F:27])[CH:21]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178517863HCID 178517863, 화합물

생성물 1

HCID 178517853HCID 178517853, 화합물수율 54.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 2631-Butanol용매

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온도
100 °C

실험 절차

A mixture of (5S)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (1.04 g, 0.00412 mol), 4-bromo-2-fluoro-1-iodobenzene (Aldrich, cat #: 283304) (1.85 g, 0.00615 mol), copper(I) iodide (Aldrich, cat #: 215554) (0.122 g, 0.000640 mol), potassium phosphate (2.63 g, 0.0124 mol) and 1,2-ethanediol (0.48 mL, 0.0086 mol) in 1-butanol (3.90 mL) was heated at 100° C. under nitrogen for 2 d. The reaction was quenched with water, and extracted with ether. The organic layers were combined, washed with water, brine, dried over Na2SO4, and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column eluting with 0 to 5% methanol in DCM to yield the desired product (950 mg, 54.2%). LC/MS m/e 425.1/427.0 (M+H)+.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on a silica gel column
  8. washeluting with 0 to 5% methanol in DCM

출처 및 근거

ORD 기록
ord-29fac59f7124407bbdb6383b02d7babb
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371323B2

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