Thiosulfuric acid, disodium salt, monohydrate → methyl 2-(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate

HRID 1912618

反応式

HRID 1912618 の反応式
[F:1][C:2]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:21])=[C:12]([CH:15]([OH:20])[C:16]([O:18][CH3:19])=[O:17])[C:13]([I:14])=[C:8]2[CH:7]=[CH:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].O>ClCCl>[F:1][C:2]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:21])=[C:12]([C:15](=[O:20])[C:16]([O:18][CH3:19])=[O:17])[C:13]([I:14])=[C:8]2[CH:7]=[CH:6]1

参加物

5

反応物 3

HCID 108762Thiosulfuric acid, disodium salt, monohydrateHCID 159087TriacetoxyperiodinaneHCID 71209168methyl 2-(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate

生成物 1

HCID 71209320methyl 2-(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of methyl 2-(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (7.95 g, 14.65 mmol) in dichloromethane (DCM) (130 mL) at 0° C. was added in two portions Dess-Martin periodinane (6.83 g, 16.11 mmol) and the mixture was stirred at ambient temperature for 30 min and then a 20% Na2S2O3/water was added and stirring at ambient temperature continued for 20 min. The mixture was diluted with dichloromethane and the organic phase was washed with NaHCO3/water (2×), dried (Na2SO4), concentrated, purified by chromatography (silica gel, EtOAc/hexanes 0-20% then 100%, product eluted at 20-60%) to provide methyl 2-(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate (5.8 g, 11.10 mmol, 76% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.54-2.64 (m, 3 H), 3.94 (s, 3 H), 5.53 (s, 2 H), 6.39 (d, J=3.71 Hz, 1 H), 6.84-6.95 (m, 1 H), 6.99 (m, 1 H) 7.10 (m, 1 H), 7.28 (d, J=3.52 Hz, 1 H); LCMS (m/z) ES+=471 (M+1).

後処理

  1. stirringstirring at ambient temperature
  2. waitcontinued for 20 min
  3. washthe organic phase was washed with NaHCO3/water (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography (silica gel, EtOAc/hexanes 0-20%
  7. wash100%, product eluted at 20-60%)

出典と根拠

ORDレコード
ord-38e2968287a9437e8f70fbacd7052442
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

関連ノート

読み込み中…