2-Bromo-4-nitrotoluene → N-(2-methyl-5-nitrophenyl)oxetan-3-amine

HRID 627

반응식

HRID 627 반응식
Cc1ccc([N+](=O)[O-])cc1Br.Cl.NC1COC1>C1CCCC1.CC(=O)O.CC(=O)O.CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.O=C([O-])[O-].[Cs+].[Cs+].[Fe].[Pd]>Cc1ccc([N+](=O)[O-])cc1NC1COC1

참가 물질

6

반응물 2

HCID 821892-Bromo-4-nitrotolueneHCID 23062080Oxetan-3-amine hydrochloride

생성물 1

HCID 80494079N-(2-methyl-5-nitrophenyl)oxetan-3-amine수율 28.82%

시약·촉매·용매 3

HCID 10796Cesium carbonate시약HCID 4144353Palladium (II) acetate촉매HCID 144543273(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-촉매

반응 조건

온도
90 °C

실험 절차

2-bromo-1-methyl-4-nitrobenzene (864 mg, 4mmol), oxetan-3-amine hydrochloride (438 mg, 4 mmol), CS2CO3 (3910 mg, 12.00 mmol), palladium(II) acetate (44.9 mg, 0.20 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t- butylphosphine (224 mg, 0.40 mmol) in 1,4-doxane was degased, inflated with Ar and heated at 90 oC for 5h. LCMS showed some product peak. Silica gel 2g was added to the mixture, evaporated all solvents in GeneVac. The sample was dry loaded for purification by ISCO (Hexane/EtOAc=100/10-100/50) N-(2-methyl-5-nitrophenyl)oxetan-3-amine (240 mg, 28.8 %) 1H NMR (400 MHz, CD2Cl2) d: 7.47 (dd, 1H), 7.14 (d, 1H), 6.98 (s, 1H), 4.99 (t, 2H), 4.63 (m, 1H), 4.46 (t, 2H), 4.20(m, 1H), 2.18 (s, 3H). LCMS: 209 [M+H]+.

출처 및 근거

ORD 기록
ord-85488250153944e595f74578eeba1555
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
출처 보기

연결된 노트

불러오는 중…