Dimethylformamide → Methyl benzo[d]isothiazole-5-carboxylate

HRID 1880429노트

반응식

HRID 1880429 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[CH:7][C:6]=2[CH:10]=1.[C:11]([O-:14])(=[O:13])C.[Na+].[CH3:16]N(C=O)C>CO.Cl[Pd]Cl>[S:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:11]([O:14][CH3:16])=[O:13])=[CH:10][C:6]=2[CH:7]=[N:8]1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 178424445-Bromo-1,2-benzothiazole

생성물 1

HCID 66920624Methyl benzo[d]isothiazole-5-carboxylate수율 5%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 887Methanol용매

실험 절차

To a solution of 1.51 g of 5-bromobenzo[d]isothiazole and 825.0 mg of 1,1′-cis(diphenylphosphino)ferrocene]dichloropalladium(II) in 35 mL methanol in a small Parr bottle was added sodium acetate (1.74 g) and DMF (543 μL). The mixture was degassed several times with nitrogen, then shaken under an atmosphere of CO (40 psi) at 50 degrees for 18 hours. The solution was filtered and concentrated. The residue was flash chromatographed (0-20% EtOAc/Haptanes gradient) to yield 61.0 mg (5%) of methyl benzo[d]isothiazole-5-carboxylate as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 3.96 (s, 3 H) 8.17 (d, J=0.98 Hz, 2 H) 8.84 (s, 1 H) 9.08 (s, 1 H); LC-MS @ 194.1 (M+1).

후처리

  1. customThe mixture was degassed several times with nitrogen
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customchromatographed (0-20% EtOAc/Haptanes gradient)

출처 및 근거

ORD 기록
ord-43197e0b7fb24e1fb0bf0f0a99e00d3f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

반응 노트

불러오는 중…