Sodium Bicarbonate → HCID 17984895、化合物

HRID 12252ノート

反応式

HRID 12252 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][C:3]=1[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].B1([C:26]2[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=2)OCCCO1.C([O-])(O)=O.[Na+]>COCCOC.CCOC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:4][C:3]=1[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 17984899(2-Amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone

生成物 1

HCID 17984895HCID 17984895、化合物収率 89%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone (600 mg, 1.83 mmol) in DME (25 mL) was added, successively, pyridine-3-boronic acid 1,3-propanediol cyclic ester (388 mg, 2.38 mmol), (tetrakistriphenylphosphine) palladium(0) (212 mg, 0.18 mmol), and 1N NaHCO3 (3.7 mL, 3.7 mmol). The resulting mixture was stared at 90° C. for 90 minutes then cooled to room temperature. The reaction mixture was diluted with EtOAc (100 mL), washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and the filtrate concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc) to afford 527 mg (89%) of the title compound as a pale orange solid: 1H NMR (CDCl3, 500 MHz) δ 8.92 (d, 1H), 8.69 (d, 1H), 8.66 (d, 1H), 8.31 (d, 1H), 8.20 (d, 1H), 7.71 (dd, 1H), 3.36 (m, 1H), 1.88 (m, 3H), 1.77 (m, 1H), 1.40-1.61 (m, 3H), 1.24-1.32 (m, 2H), 0.89 (m, 1H).

後処理

  1. washwashed with water (50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-e16e26ba504e42cea01239161cdd285d
出典データセット
uspto-grants-2010_06
特許番号
US07727992B2

反応ノート

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