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Sodium Iodide → 3-(4-(benzyloxy)phenylsulfonyl)-N-mesityl-6-methylpyridin-2-amine

HRID 1796329
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HRID 1796329 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.CCOC(C)=O>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([C:5]2[C:6]([NH:8][C:9]3[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=3[CH3:17])=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:20])=[O:19])=[CH:26][CH:25]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 112112464-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol

생성물 1

HCID 112252363-(4-(benzyloxy)phenylsulfonyl)-N-mesityl-6-methylpyridin-2-amine수율 92.2%

시약·촉매·용매 2

HCID 6342
Acetonitrile
용매
HCID 8857Ethyl Acetate용매

실험 절차

4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol from Example 10 (300 mg, 0.78 mmol), benzyl bromide (0.10 mL, 0.84 mmol), K2CO3 (129 mg, 0.93 mmol) and NaI (20 mg, 0.13 mmol) was heated at reflux in acetonitrile (5 mL) for 15 h. Then it was diluted with EtOAc (15 mL), filtered through florisil and the filtrate was stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give the product as a solid (340 mg), mp 158–160° C. mass spec. (AP+): m/z 473 (M+1).

후처리

  1. filtrationfiltered through florisil
  2. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent

출처 및 근거

ORD 기록
ord-dd859d8d170f4ceebe005eadf0625f91
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07030145B2

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