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

HRID 1880429ノート

反応式

HRID 1880429 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 66920624Methyl benzo[d]isothiazole-5-carboxylate収率 5%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-43197e0b7fb24e1fb0bf0f0a99e00d3f
出典データセット
uspto-grants-2012_11
特許番号
US08318762B2

反応ノート

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