5-Nitro-2-pyridin-4-yl-benzooxazole → 2-Pyridin-4-yl-benzooxazol-5-ylamine

HRID 64234

반응식

HRID 64234 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:18]=1)([O-])=O>C(OCC)(=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[N:9][C:8]=2[CH:18]=1

참가 물질

4

반응물 1

HCID 127818735-Nitro-2-pyridin-4-yl-benzooxazole

생성물 1

HCID 7360092-Pyridin-4-yl-benzooxazol-5-ylamine수율 86%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584119Ethylacetate methanol용매

실험 절차

To a solution of 5-nitro-2-(pyridine-4-yl) benzo[d]oxazole 3 (600 mg, 2.48 mmol) in ethyl acetate/MeOH (10 mL) was added catalytic amount of 10% Pd—C under hydrogen atmosphere and stirred it for 6 h at room temperature and filtered by flash column chromatography (100% ethyl acetate) to afford 5-amino-2-(pyridine-4-yl) benzo[d]oxazole 4 (450 mg, 86%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 6.78 (dd, J1=12 Hz, J2=2.4 Hz, 1H), 7.07 (d, J=2 Hz, 1H), 7.40 (d, J=4.8 Hz, 1H), 8.05 (dd, J1=8 Hz, J2=1.6 Hz, 2H), 8.79 (dd, J1=4 Hz, J2=1.6 Hz, 2H), 3.78 (s, 2H).

후처리

  1. filtrationfiltered by flash column chromatography (100% ethyl acetate)

출처 및 근거

ORD 기록
ord-c6393ad273be433396fbda3e97ce6e58
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447134B2

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