Triethylamine → [6-(5-Ethoxymethoxy-benzofuran-2-yl)-2-nitro-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester

HRID 217210ノート

反応式

HRID 217210 の反応式
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](B(O)O)=[CH:11][C:10]=2[CH:17]=1)[CH3:2].[C:18]([O:22][C:23](=[O:36])[N:24]([C:26]1[C:27]([N+:33]([O-:35])=[O:34])=[N:28][C:29](Br)=[CH:30][CH:31]=1)[CH3:25])([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC>C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([O:22][C:23](=[O:36])[N:24]([C:26]1[C:27]([N+:33]([O-:35])=[O:34])=[N:28][C:29]([C:12]2[O:13][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][O:3][CH2:1][CH3:2])=[CH:17][C:10]=3[CH:11]=2)=[CH:30][CH:31]=1)[CH3:25])([CH3:21])([CH3:19])[CH3:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 461839705-Ethoxymethoxy-benzofuran-2-boronic acidHCID 46855854(6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 46183969[6-(5-Ethoxymethoxy-benzofuran-2-yl)-2-nitro-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester収率 84.3%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a degassed solution of 5-ethoxymethoxy-benzofuran boronic acid (4) (140 mg, 0.593 mmol) in ethanol (10 mL), (6-bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester (7) (151 mg, 0.455 mmol), Pd(PPh3)2Cl2 (42 mg, 0.059 mmol) and Et3N (127 μL, 0.909 mmol) were added. The reaction mixture was stirred at 100° C. for 30 minutes in a microwave reactor. Volatiles were removed under reduced pressure. The residue was diluted with water (15 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash column chromatography using 20% ethyl acetate in hexane. Evaporation of solvent gave title compound 8 (170 mg) as a pale yellow solid.

後処理

  1. customVolatiles were removed under reduced pressure
  2. additionThe residue was diluted with water (15 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography
  8. customEvaporation of solvent

出典と根拠

ORDレコード
ord-9330242a3d944ab085525643d432e896
出典データセット
uspto-grants-2012_06
特許番号
US08193363B2

反応ノート

読み込み中…