Dichloromethane → 4-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1865054노트

반응식

HRID 1865054 반응식
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:25])[C:17]([CH2:23][CH3:24])=[C:18]([C:21]#[N:22])[C:19]=1I)=[O:14])[CH3:11].C(Cl)Cl.C(N(CC)CC)C>C(#N)C.O>[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:25])[C:17]([CH2:23][CH3:24])=[C:18]([C:21]#[N:22])[C:19]=1[B:4]1[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]1)=[O:14])[CH3:11]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 57975348HCID 57975348, 화합물

생성물 1

HCID 579748024-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Add 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.87 mL, 6.0 mmol) to 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.0 g, 3.0 mmol, prepared in prepared in Preparation 38), [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complex with methylene chloride (1:1) (0.122 g, 0.15 mmol), and triethylamine (1.25 mL, 9.0 mmol) in acetonitrile and heat to reflux. After 3 hours, cool and pour into water. Extract with ethyl acetate. Wash the combined organics with water and brine, dry over magnesium sulfate, filter and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with ethyl acetate:hexanes to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 4.33 (q, 2H), 3.84 (s, 3H), 2.80 (q, 2H), 1.40 (s, 12H), 1.46 (t, 3H), 1.22 (t, 3H).

후처리

  1. temperatureheat to reflux
  2. temperaturecool
  3. extractionExtract with ethyl acetate
  4. washWash the combined organics with water and brine
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography (silica gel)
  9. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-5f4c73361e964e13987ed25e8e5423eb
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625932B2

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