Dichloromethane → HCID 178519325、化合物

HRID 707466ノート

反応式

HRID 707466 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[NH:12]1[C:16](B(O)O)=[CH:15][CH:14]=[N:13]1.COCCOC.ClCCl>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(N(CC)CC)C>[N+:7]([C:6]1[S:5][C:4]([CH:10]=[O:11])=[CH:3][C:2]=1[C:16]1[CH:15]=[CH:14][NH:13][N:12]=1)([O-:9])=[O:8]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 112519791H-Pyrazole-5-boronic acidHCID 218862814-Bromo-5-nitrothiophene-2-carbaldehyde

生成物 1

HCID 178519325HCID 178519325、化合物収率 100.4%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

A flask containing 4-bromo-5-nitrothiophene-2-carbaldehyde (1.00 g, 4.24 mmol), (1H-pyrazol-5-yl)boronic acid (510 mg, 4.56 mmol), ethyleneglycol dimethyl ether (20 mL), triethylamine (1.80 mL), water (2.00 mL) and bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (340 mg, 0.42 mmol) was evacuated and purged with nitrogen twice, then heated at 80° C. under nitrogen for 4 h. The reaction was cooled to room temperature, poured into a saturated solution of ammonium chloride (20 mL), extracted with ethyl acetate (3×10 mL), combined organics washed with a saturated solution of ammonium chloride (30 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with ethyl acetate in hexanes, to yield 5-nitro-4-(1H-pyrazol-3-yl)thiophene-2-carbaldehyde as a yellow oil (950 mg, 28%). 1H NMR (400 MHZ, DMSO-d6) δ 6.99 (s, 1H), 7.94 (s, 1H), 8.42 (s, 1H), 10.07 (s, 1H).

後処理

  1. customwas evacuated
  2. custompurged with nitrogen twice
  3. temperatureThe reaction was cooled to room temperature
  4. additionpoured into a saturated solution of ammonium chloride (20 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. washcombined organics washed with a saturated solution of ammonium chloride (30 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography
  10. washeluting with ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-ceebab437e3f454a9bd99cf7b5456914
出典データセット
uspto-grants-2015_11
特許番号
US09175010B2

反応ノート

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