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 1865054ノート

反応式

HRID 1865054 の反応式
[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]

参加物

7

反応物 4

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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5f4c73361e964e13987ed25e8e5423eb
出典データセット
uspto-grants-2009_12
特許番号
US07625932B2

反応ノート

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