Potassium tert-butoxide → HCID 59603103, 화합물

HRID 2068707노트

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HRID 2068707 반응식
[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([CH3:27])=[CH:15][C:14]=1Br)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>O1CCOCC1.CCOC(C)=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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:20]([O:19][C:17]1[C:16]([CH3:27])=[CH:15][C:14]2[S:11][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:12][C:13]=2[CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 2

HCID 23665647Potassium tert-butoxideHCID 59603075HCID 59603075, 화합물

생성물 1

HCID 59603103HCID 59603103, 화합물수율 61%

시약·촉매·용매 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of 1-benzoyl-3-(5-benzyloxy-2-bromo-4-methyl-phenyl)-thiourea II (1.0 g, 2.20 mmol) in 1,4-dioxane (30 mL) was added sequentially Pd2(dba)3 (0.12 g, 0.12 mmol), dppf (0.07 g, 0.12 mmol) and KOtBu (0.75 g, 3.30 mmol) at room temperature under N2 atmosphere. The resulting reaction mixture was heated at 80° C. for 6 h. After completion of reaction (TLC monitoring), the reaction mixture was diluted with EtOAc and filtered through celite bed-bed. The filtrate was concentrated and purified over silica gel (100-200 M, 20% EtOAc-Hexane) to obtain the desired product (0.50 g, 61%). 1H NMR (400 MHz, DMSO-d6): δ 2.31 (s, 3H), 5.23 (s, 2H), 7.33 (m, 1H), 7.39 (m, 3H), 7.52 (m, 2H), 7.54 (m, 2H), 7.64 (m, 1H), 7.76 (s, 1H), 8.13 (d, J=7.60 Hz, 2H) and 12.77 (br s, 1H). MS: 375.19 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. customAfter completion of reaction (TLC monitoring)
  3. filtrationfiltered through celite bed-bed
  4. concentrationThe filtrate was concentrated
  5. custompurified over silica gel (100-200 M, 20% EtOAc-Hexane)

출처 및 근거

ORD 기록
ord-4eb605fc06f84ef7885e9178de426cd7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299065B2

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