Sodium Bicarbonate → (S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate

HRID 1485753노트

반응식

HRID 1485753 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:15])[CH2:6][NH:5]2.CC1(C)C(C)(C)OB([C:24]2[CH:44]=[CH:43][C:27]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[O:29])=[CH:26][CH:25]=2)O1.C(=O)(O)[O-].[Na+]>O1CCOCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:24]3[CH:44]=[CH:43][C:27]([C:28]([N:30]4[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:34][CH2:35]4)=[O:29])=[CH:26][CH:25]=3)=[CH:11][CH:10]=2)[NH:5][CH2:6][C@@H:7]1[CH3:15])(=[O:14])[CH3:13]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 17749917(4-(4-BOC-piperazine-1-carbonyl)phenyl)boronic acid pinacol esterHCID 118078861(S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

생성물 1

HCID 118079960(S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate수율 83%

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.200 g, 0.743 mmol), tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)piperazine-1-carboxylate (0.340 g, 0.817 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.052 g, 0.074 mmol), and sodium bicarbonate (1 M in water, 1.5 mL, 1.5 mmol) in 1,4-dioxane (3.7 mL) was heated at 80° C. for 16 h. The reaction mixture was filtered through Celite and concentrated to afford an orange oil. This material was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford (S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate (0.294 g, 83%) as an off-white solid. MS (ESI, pos. ion) m/z 479.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto afford an orange oil
  4. customThis material was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-e42b6be38fcf4445828ec1a617153f07
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422281B2

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