Dichloromethane → HCID 178519325, 화합물

HRID 707466

반응식

HRID 707466 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 178519325HCID 178519325, 화합물수율 100.4%

시약·촉매·용매 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ceebab437e3f454a9bd99cf7b5456914
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175010B2

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