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

HRID 1877934
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HRID 1877934 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
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참가 물질

7

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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 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 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, 3 H), 2.69-2.82 (m, 1 H), 3.07-3.22 (m, 3 H), 4.02-4.22 (m, 2 H), 5.92-6.03 (m, 1 H), 7.27 (d, J=7.8 Hz, 1 H), 7.31 (s, 1 H), 7.36 (dd, J=7.8, 1.5 Hz, 1 H), 7.43 (d, J=1.3 Hz, 1 H), 8.68 (s, 1 H).

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-f2ec075e95d04fa5b068c6912dbb3e18
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08314097B2

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