Hydrochloric Acid → HCID 21947829、化合物

HRID 2184471ノート

反応式

HRID 2184471 の反応式
I[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[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>[Cl:11][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([O:12][CH3:13])=[CH:3][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[F:14]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 167918585-Chloro-4-iodo-2-methoxybenzoic acid

生成物 1

HCID 21947829HCID 21947829、化合物収率 70.9%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-iodo-5-chloro-2-methoxy benzoic acid of Example 20, Step A (3.72 g, 19.1 mmol) in N,N-dimethylformamide (20 mL) was added 2-fluorophenyl boronic acid (5.0 g, 35.7 mmol) and potassium carbonate (14.8 g, 107 mmol). This mixture was purged with nitrogen and then treated with a catalytic amount of tetrakis(triphenylphosphine) palladium(0) (0.688 g, 0.59 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was flash chromatographed on acid washed silica using a 10 to 50% gradient of diethyl ether in hexane to provide the desired title compound (3.8 g) as a white solid.

後処理

  1. customThis mixture was purged with nitrogen
  2. temperatureThe reaction was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customchromatographed on acid
  11. washwashed silica using a 10 to 50% gradient of diethyl ether in hexane

出典と根拠

ORDレコード
ord-62df3efc4ee5447483aa817a9daa52f8
出典データセット
uspto-grants-2005_05
特許番号
US06900200B2

反応ノート

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