Triphenylphosphine → 4-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine

HRID 872403노트

반응식

HRID 872403 반응식
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][C:40]=1[CH2:41][CH2:42]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:42][CH2:41][C:40]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[NH2:34])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 3438294-Nitro-1-naphtholHCID 5363146Diisopropyl azodicarboxylateHCID 468355964-Pyridineethanol, 3-amino-

생성물 1

HCID 584167784-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-nitronaphthol (0.95 g, 5.00 mmol), PPh3 (1.97 g, 7.50 mmol) and 2-(3-aminopyridin-4-yl)ethanol (16) (1.04 g, 7.50 mmol) in THF (20 mL) was added dropwise DIAD (590 μl, 3.75 mmol) at −15° C. The mixture was stirred for 1 hr at RT and the volatiles removed in vacuo. The residues was absorbed on silica (20 g) and purified by column chromatography (80 g) gradient elution with 50-100% EtOAc/iso-hexane and final elution with 5% MeOH/EtOAc to give 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine a yellow solid (17) (1.36 g, 88%): m/z 310 (M+H)+ (ES+).

후처리

  1. customthe volatiles removed in vacuo
  2. customThe residues was absorbed on silica (20 g)
  3. custompurified by column chromatography (80 g) gradient elution with 50-100% EtOAc/iso-hexane
  4. washfinal elution with 5% MeOH/EtOAc

출처 및 근거

ORD 기록
ord-18e3f3df3ceb4e1ba7c8ddb85952dc7a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975285B2

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