Water → HCID 69020209、化合物

HRID 1865094ノート

反応式

HRID 1865094 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1I)=[O:5])[CH3:2].[F:17][C:18]1[CH:39]=[CH:38][CH:37]=[CH:36][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].O.O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1[C:24]1[CH:23]=[CH:22][C:21]([O:20][C:19]2[CH:36]=[CH:37][CH:38]=[CH:39][C:18]=2[F:17])=[CH:26][CH:25]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 2735133Sodium Carbonate MonohydrateHCID 57975348HCID 57975348、化合物HCID 579753882-(4-(2-Fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 69020209HCID 69020209、化合物

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

Combine 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in preparation 38, 0.46 mmol), 2-[4-(2-fluoro-phenoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (1.3 Eq), tetrakis(triphenylphosphine)-palladium(0) (0.1 Eq) and 2.0 M sodium carbonate/water (6.5 Eq) in 1,4-dioxane (10 mL) and heat at −80° C. to 90° C. overnight. Let the reaction cool to room temperature and pour into water. Extract the quenched reaction mixture with ethyl acetate. Combine the organic extracts, wash with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum. Purify the residue by silica gel chromatography (Chromatotron™) eluting with hexane/ethyl acetate 4:1 to provide the final title compound, 4-cyano-5-ethyl-3-[4-(2-fluoro-phenoxy)-phenyl]-1-methyl-1H-pyrole-2-carboxylic acid ethyl ester, as a tan solid. Mass spectrum (m/e): 393.1 (M*+1): (Bruker 300) 1H NMR (CDCl3) δ 7.27-7.31 (3H, d), 7.07-7.20 (3H, m), 6.95-6.99 (2H, d), 4.04-4.11 (2H, dd), 3.84-3.88 (3H, s), 2.74-2.86 (2H, dd), 1.23-1.34 (3H, t), 1.00-1.06 (3H, t).

後処理

  1. extractionExtract
  2. customthe quenched reaction mixture with ethyl acetate
  3. washwash with water
  4. dry with materialdry over potassium carbonate
  5. filtrationfilter
  6. concentrationconcentrate under reduced vacuum
  7. customPurify the residue by silica gel chromatography (Chromatotron™)
  8. washeluting with hexane/ethyl acetate 4:1

出典と根拠

ORDレコード
ord-3555ca1260d744309dc89535a77d5010
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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