7-Chloro-2-iodothieno(3,2-b)pyridine → 6-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1676393노트

반응식

HRID 1676393 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12

참가 물질

5

반응물 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 673463376-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

생성물 1

HCID 673468456-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 7961Bromobenzene용매

실험 절차

A mixture of 6-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.078 g, 0.186 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.050 g, 0.169 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.021 g, 0.169 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for two days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 30:1 CH2Cl2/MeOH. The product was obtained (35 mg; 36%) as a yellow solid. LRMS (APCI pos) m/e 583 (M+1).

후처리

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove as much bromobenzene as possible and
  4. customthen purified directly by flash column chromatography
  5. washeluting with 30:1 CH2Cl2/MeOH
  6. customThe product was obtained (35 mg; 36%) as a yellow solid

출처 및 근거

ORD 기록
ord-b91f38f2304e41f59d98ac96f778fc51
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003662B2

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