Hydrochloric Acid → HCID 89443880、化合物

HRID 1771714ノート

反応式

HRID 1771714 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.O>[C:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:12]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 219425423-Bromo-5-cyanobenzoic acid

生成物 1

HCID 89443880HCID 89443880、化合物収率 56.5%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-Bromo-5-cyano-benzoic acid (2 g, 8.8 mmol, 1 eq) and 3-fluorophenylboronic acid (1.6 g, 11.5 mmol, 1.3 eq) in DMF (100 mL) under nitrogen were added Pd(PPh3)4 (500 mg, 0.44 mmol, 0.05 eq) and K2CO3 (3.6 g, 26.4 mmol, 3 eq). The solution was heated at 100° C. overnight, then water and EtOAc were added. The aqueous layer was acidified by addition of diluted HCl and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2Cl2:MeOH, 25:1) to give the title compound as a white solid (1.2 g, 56%).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (CH2Cl2:MeOH, 25:1)

出典と根拠

ORDレコード
ord-284236a7799b4889a30a0bebcbb01c06
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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