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1,4-Dioxane → HCID 58994547、化合物

HRID 1508114
ノート
印刷プレビュー

反応式

HRID 1508114 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:10])=[CH:4][C:3]=1Br.C1(P(C2CCCCC2)C2C=CC=C[C:26]=2[C:31]2[C:36](OC)=[CH:35][CH:34]=[CH:33][C:32]=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOC[CH2:56]1>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]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:10])=[CH:4][C:3]=1[C:34]1[CH2:33][CH2:32][C:31]([CH3:26])([CH3:56])[CH2:36][CH:35]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58994585HCID 58994585、化合物

生成物 1

HCID 58994547HCID 58994547、化合物収率 28%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a flask containing 2-(4-amino-3-bromo-phenyl)-N-(2-dimethylamino-ethyl)-acetamide (as prepared in the previous step, 83 mg, 0.27 mmol), tris(dibenzylideneacetone)dipalladium (0) (4.0 mg, 0.0080 mmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (5.6 mg, 0.010 mmol) and K3PO4 (0.17 g, 0.82 mmol) was charged dioxane (3 mL) and the reaction was heated to 100° C. for 48 h. At this time the reaction was diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by preparative TLC (10% MeOH—CHCl3) to afford 26 mg (28%) of the title compound as a tan solid. 1H-NMR (CDCl3; 400 MHz): δ 6.85 (dd, 1H, J=8.0, 2.1 Hz), 6.79 (d, 1H, J=2.1 Hz), 6.59 (d, 1H, J=8.0 Hz), 6.01 (br s, 1H), 5.60 (m, 1H), 3.66 (br s, 2H), 3.35 (s, 2H), 3.23-3.18 (m, 2H), 2.27 (t, 1H, J=6.1 Hz), 2.20-2.14 (m, 2H), 2.09 (s, 6H), 1.90-1.88 (m, 2H), 1.44 (t, 2H, J=6.3 Hz), 0.92 (s, 6H).

後処理

  1. washwashed with water (25 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by preparative TLC (10% MeOH—CHCl3)

出典と根拠

ORDレコード
ord-db68b4a15c7c4fbdad4908f937a2fc1b
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221797B2

反応ノート

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