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

HRID 2205111

반응식

HRID 2205111 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-320bf4d8c83d42f4b42d168b923f589e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09370522B2

연결된 노트

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