Potassium tert-butoxide → HCID 59603103、化合物

HRID 2068707ノート

反応式

HRID 2068707 の反応式
[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

参加物

7

反応物 2

HCID 23665647Potassium tert-butoxideHCID 59603075HCID 59603075、化合物

生成物 1

HCID 59603103HCID 59603103、化合物収率 61%

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-4eb605fc06f84ef7885e9178de426cd7
出典データセット
uspto-grants-2012_10
特許番号
US08299065B2

反応ノート

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