Cyclopropylamine → HCID 28536514, 화합물

HRID 1048984

반응식

HRID 1048984 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:13]1([NH:16][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:15][CH2:14]1

참가 물질

6

반응물 3

HCID 69828CyclopropylamineHCID 2926594-Iodo-3-nitroanisoleHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

생성물 1

HCID 28536514HCID 28536514, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 1-iodo-4-methoxy-2-nitrobenzene (0.2 g, 0.0007 mol) in toluene (6.0 mL) was added cyclopropylamine (0.068 ml, 0.0008 mol) potassium tert-butoxide (0.094 g, 0.0098 mol) and Ruphos (0.049 g, 0.00010 mol) at room temperature and purged with argon for 15 min. Then Pd2(dba)3 (0.064 g, 0.00007 mol) was added and resulting mixture was heated to 100° C. in CEM microwave for 30 min. After the reaction was complete the reaction mixture was filtered through CELITE® bed and the bed was thoroughly washed with ethyl acetate. The filtrate was washed with water brine dried over Na2SO4 and concentrated under reduced pressure to afford the crude compound, which was purified by column chromatography to obtain title compound cyclopropyl-(4-methoxy-2-nitro-phenyl)-amine (yellow solid). C10H12N2O3; 1H NMR (400 MHz, CDCl3), δ: 7.98 (s, 1H), 7.60 (d, J=2.8 Hz, 1H), 7.30 (s, 1H), 7.19-7.16 (m, 1H), 4.12 (q, J=6.8, 1H), 3.80 (s, 1H), 0.89 (dd, J1=12.0 Hz, J2=6.0 Hz, 2H), 0.64 (t, J=6.8 Hz, 2H). MS (M+1): 209.1.

후처리

  1. custompurged with argon for 15 min
  2. customresulting mixture
  3. filtrationwas filtered through CELITE® bed
  4. washthe bed was thoroughly washed with ethyl acetate
  5. washThe filtrate was washed with water brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound, which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-8824a40aa1f342a4af373046508dcd01
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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