Potassium Carbonate → 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole

HRID 506109ノート

反応式

HRID 506109 の反応式
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18](F)(F)F)[CH:15]=2)[CH:10]=[C:9]1B(O)O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][CH2:35][CH2:34][S:33]2(=[O:38])=[O:37])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:36][CH2:35][CH2:34][S:33]2(=[O:38])=[O:37])=[CH:30][CH:31]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 147632212-(4-Iodophenyl)isothiazolidine-1,1-dioxideHCID 57355675(1-(tert-Butoxycarbonyl)-6-(trifluoromethoxy)-1H-indol-2-yl)boronic acid

生成物 1

HCID 594306781-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1-Boc-6-trifluoromethoxyindole-2-boronic acid prepared above (0.74 g, 2.1 mmol), 2-(4-iodophenyl)isothiazolidine-1,1-dioxide (0.76 g, 2.4 mmol), and PdCl2(dppf) (0.08 g, 0.1 mmol) in DMF (6.0 mL), is added K2CO3 solution (3.2 mL, 2.0 M, 6.4 mmol). The mixture is stirred at room temperature overnight and then poured into ice-water (100 mL). The precipitate is collected and washed with water and purified by flash column chromatography (silica gel, DCM/EtOAc, 9/1) to furnish 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole, which is treated with 50% TFA in DCM (15 mL) at room temperature for 1 h. After the removal of the volatiles, the residue is carefully stirred with saturated NaHCO3 for 0.5 h. The precipitate is collected via filtration and washed thoroughly with water and dried to provide essentially pure 1-H-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-trifluoromethoxyindole.

後処理

  1. customThe precipitate is collected
  2. washwashed with water
  3. custompurified by flash column chromatography (silica gel, DCM/EtOAc, 9/1)

出典と根拠

ORDレコード
ord-fae868d810be4b12948cee1c2132e507
出典データセット
uspto-grants-2010_08
特許番号
US07781478B2

反応ノート

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