Iodine chloride → 3-(2-Fluoro-4-iodo-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester

HRID 2264917노트

반응식

HRID 2264917 반응식
[CH3:1][O:2][C:3]([C:5]1[N:13]([CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[C:6]=1[NH:27][C:28]1[CH:33]=[CH:32][C:31]([Si](C)(C)C)=[CH:30][C:29]=1[F:38])=[O:4].[I:39]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:13]([CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[C:6]=1[NH:27][C:28]1[CH:33]=[CH:32][C:31]([I:39])=[CH:30][C:29]=1[F:38])=[O:4]

참가 물질

4

반응물 2

HCID 24640Iodine chlorideHCID 595966283-(2-Fluoro-4-trimethylsilanyl-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 595965243-(2-Fluoro-4-iodo-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester (1.78 g, 3.20 mmol) in DCM (35 mL) was added iodine monochloride (1M in DCM, 6.40 mL) dropwise over 10 minutes. The mixture was stirred for 1 hour then quenched by the addition of saturated sodium thiosulphate solution. The solution was partitioned between ethyl acetate and an saturated solution of sodium hydrogencarbonate. The organic layer was separated, washed with water then brine, dried (Na2SO4), filtered and evaporated to give a residue. The residue was purified by flash chromatography (Si-PPC, cyclohexane:ethylacetate, gradient 100:0 to 0:100) to provide the title compound as a yellow oil (1.52 g, 79%). LCMS (method B): RT=3.47 min, M+H+=612.

후처리

  1. customthen quenched by the addition of saturated sodium thiosulphate solution
  2. customThe solution was partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue
  9. customThe residue was purified by flash chromatography (Si-PPC, cyclohexane:ethylacetate, gradient 100:0 to 0:100)

출처 및 근거

ORD 기록
ord-5ae5dea626134fcda31ab6c9229740ed
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855216B2

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