4-chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine → 5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

HRID 2241296노트

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HRID 2241296 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:23])[N:11]([CH3:22])[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[N:32]=[C:33]([I:34])[C:26]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:23])[N:11]([CH3:22])[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[N:32]=[C:33]([I:34])[C:26]=12

참가 물질

5

반응물 2

HCID 672207314-chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridineHCID 673501215-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

생성물 1

HCID 685142125-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one수율 77.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 7961Bromobenzene용매

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온도
150 °C

실험 절차

A mixture of 5-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.009 g, 0.03 mmol, prepared in Example 45, step F), 4-chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (0.010 g, 0.0250 mmol) and DMAP (0.006 g, 0.05 mmol) in bromobenzene (0.300 mL) under N2 was stirred at 150° C. for 3 days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 10:1 CH2Cl2/MeOH. The desired product (0.013 g, 76%) was obtained as a yellow solid. LRMS (APCI pos) m/e 675 (M+1).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove as much bromobenzene as possible and
  3. customthen purified directly by flash column chromatography
  4. washeluting with 10:1 CH2Cl2/MeOH

출처 및 근거

ORD 기록
ord-d43e8d7cb84047bd8050e1e2a0e647fd
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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