Ethanol → 4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-ethoxybenzonitrile

HRID 76873노트

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HRID 76873 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:14]2[CH:15]=[N:16][CH:17]=[C:13]2[CH2:12][CH2:11]1)[C:5]#[N:6].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:70][CH2:71][OH:72]>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].COCCOC>[CH:17]1[N:16]=[CH:15][N:14]2[CH:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[O:72][CH2:71][CH3:70])[CH2:11][CH2:12][C:13]=12

참가 물질

7

반응물 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 588270573-bromo-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

생성물 1

HCID 588271654-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-ethoxybenzonitrile

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

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온도
135 °C

실험 절차

A solution of 3-bromo-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (0.090 g, 0.312 mmol) given in Example 3 (table 2), Pd2(dba)3 (0.029 g, 0.031 mmol), BINAP (0.039 g, 0.062 mmol), Cs2CO3 (0.204 g, 0.625 mmol), EtOH (0.091 mL, 1.54 mmol), and DME (4 mL) is heated in a microwave reactor at 135° C. for 1.5 h. At that point LCMS showed consumption of the starting material. The mixture is filtered and then the filtrate is concentrated. The residue is then purified by flash chromatography (0-10% MeOH/DCM) give 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-ethoxybenzonitrile. MS (ESI) m/z 254.1 (M+H); 1H NMR (400 MHz, MeOD) (TFA salt) δ ppm 1.32 (t, J=6.9 Hz, 3H), 2.69-2.82 (m, 1H), 3.07-3.22 (m, 3H), 4.02-4.22 (m, 2H), 5.92-6.03 (m, 1H), 7.27 (d, J=7.8 Hz, 1H), 7.31 (s, 1H), 7.36 (dd, J=7.8, 1.5 Hz, 1H), 7.43 (d, J=1.3 Hz, 1H), 8.68 (s, 1H).

후처리

  1. customconsumption of the starting material
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is then purified by flash chromatography (0-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-25e1ecea06854028a6e26e4fd791b15b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835646B2

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