Triethylamine → HCID 18449401, 화합물

HRID 1921194노트

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HRID 1921194 반응식
Br[C:2]1[N:3]=[C:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:8]2=[O:24])[S:5][CH:6]=1.C(N(CC)CC)C>CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:20]([O:19][C:17](=[O:18])[CH2:16][N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]([C:4]2[S:5][CH:6]=[C:2]([C:17]([O:19][CH3:20])=[O:18])[N:3]=2)[C:8]1=[O:24])([CH3:23])([CH3:22])[CH3:21]

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 86607786tert-Butyl [3-(4-bromo-1,3-thiazol-2-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

생성물 1

HCID 18449401HCID 18449401, 화합물

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 887Methanol용매

실험 절차

To a suspension of tert-butyl [3-(4-bromo-1,3-thiazol-2-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate from Step A (250 mg, 0.609 mmol) and triethylamine (0.850 mL, 6.09 mmol) in MeOH (5 mL) was added bis(triphenylphosphine)palladium (II) chloride (86.0 mg, 0.122 mmol). The reaction mixture was heated at reflux under an atmosphere of carbon monoxide (ca. 1 atm) for 48 h, then partitioned between CHCl3 (20 mL) and saturated aqueous NaHCO3 (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 60:40, to give the title compound. MS: m/z=412 (M+23).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under an atmosphere of carbon monoxide (ca. 1 atm) for 48 h
  3. custompartitioned between CHCl3 (20 mL) and saturated aqueous NaHCO3 (5 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-00e807f4c5c64700ba743aa76f6f13a5
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173655B2

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