Ethyl Acetate → 4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

HRID 1510042노트

반응식

HRID 1510042 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CC(C)([O-])C.[Na+].C(OCC)(=O)C>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:18]([O:22][C:23]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:17][CH2:16][C:11]4([O:15][CH2:14][CH2:13][O:12]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 121693418-(4-Bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decaneHCID 16740533Tert-butyl 1,2,3,4-tetrahydroquinoxaline-1-carboxylateHCID 23676156Sodium t-butoxide

생성물 1

HCID 668631744-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester수율 58.4%

시약·촉매·용매 3

HCID 83681Tris(1,1-dimethylethyl)phosphine촉매HCID 167845palladium(II) acetate촉매HCID 7237O-Xylene용매

반응 조건

온도
150 °C

실험 절차

0.31 g of 8-(4-bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane is placed in 5 ml of anhydrous o-xylene. 0.24 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is added, then 0.15 g of sodium tert-butoxide is added, followed by 0.009 g of palladium acetate, and then the addition is completed with 0.0084 g of tri(tert-butyl)phosphine. The reaction mixture is heated at 150° C. for 4 h, then the heating is halted and the mixture is brought back to ambient temperature. Ethyl acetate is added and the mixture is washed twice with water and then twice with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a heptane/ethyl acetate (4/1) solvent mixture. 0.27 g of 4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is obtained.

후처리

  1. additionthe addition
  2. customis brought back to ambient temperature
  3. washthe mixture is washed twice with water
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product obtained
  7. customis chromatographed on silica gel, elution

출처 및 근거

ORD 기록
ord-3f41906759de48d384737604ae47ad72
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211892B2

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