tert-Butyl piperazine-1-carboxylate → HCID 67125779, 화합물

HRID 2042408노트

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HRID 2042408 반응식
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH3:11])=[CH:4][N:3]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:11][C:5]1[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[N:3][CH:4]=1

참가 물질

8

반응물 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 14372148HCID 14372148, 화합물HCID 23676156Sodium t-butoxide

생성물 1

HCID 67125779HCID 67125779, 화합물수율 50%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A stirred mixture of commercially available 4-chloro-7-methyl-furo[3,2-c]pyridine (2.5 g, 14.9 mmol), tert-butyl piperazine-1-carboxylate (3.33 g, 17.9 mmol), sodium tert.-butoxide (2.01 g, 20.9 mmol), palladium(II) acetate (335 mg, 1.49 mmol) and 2-(di-tert.-butylphosphino) biphenyl (445 mg, 1.49 mmol) in toluene (33.0 ml) was heated for 16 h at 100° C. The mixture was cooled and water (10 ml) was added. The mixture was extracted with ethylacetate (2×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product (5.9 g) was further purified by flash chromatography on silica gel (10% to 100% ethyl acetate in heptane) to yield tert-butyl 4-(7-methyl-furo[3,2-c]pyridin-4-yl)-piperazine-1-carboxylate as a yellow solid (2.35 g, 50%), MS (ISP) m/z=318.3 [(M+H)+], mp 108.5° C.

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethylacetate (2×20 ml)
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product (5.9 g) was further purified by flash chromatography on silica gel (10% to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-44b73e40746d45a6b0b319d5d5cacc78
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586579B2

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