Hydrochloric Acid → 3-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 2205111ノート

反応式

HRID 2205111 の反応式
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[C:30](B(O)O)[C:25]=2[O:24][CH2:23]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:2]3[C:3]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:4][C:5]4[C:10]([N:11]=3)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=4)=[CH:30][C:25]=2[O:24][CH2:23]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 41926592,3-Methylenedioxyphenyl boronic acidHCID 86667202HCID 86667202、化合物

生成物 1

HCID 867181103-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid収率 41.1%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

A suspension of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (80 mg, 0.23 mmol, 1.00 equiv), benzo[d][1,3]dioxol-4-ylboronic acid (59 mg, 0.36 mmol, 1.50 equiv), tricyclohexylphosphine (9 mg, 0.03 mmol, 0.14 equiv), Pd2(dba)3 (13 mg, 0.01 mmol, 0.06 equiv), and K3PO4 (149 mg, 0.80 mmol, 3.00 equiv). in dioxane/H2O (1/0.5 mL) in a 10-mL sealed tube was allowed to react, with stifling, overnight at 95° C. The pH value of the solution was adjusted to 7 with HCl (1N). Purification via silica gel column (dichloromethane:methanol (1:10)) afforded 35 mg (40%) of 3-(benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

後処理

  1. customto react
  2. customovernight
  3. customat 95° C
  4. customPurification via silica gel column (dichloromethane:methanol (1:10))

出典と根拠

ORDレコード
ord-320bf4d8c83d42f4b42d168b923f589e
出典データセット
uspto-grants-2016_06
特許番号
US09370522B2

反応ノート

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