3-Bromopyridine-2-carbonitrile → 3-[3-(7-Methylimidazo[1,2-a]pyrimidin-3-yl)phenyl]pyridine-2-carbonitrile

HRID 478241

반응식

HRID 478241 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.Br[C:27]1[C:28]([C:33]#[N:34])=[N:29][CH:30]=[CH:31][CH:32]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([C:27]4[C:28]([C:33]#[N:34])=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1

참가 물질

3

반응물 2

HCID 8176943-Bromopyridine-2-carbonitrileHCID 180012787-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine

생성물 1

HCID 99445533-[3-(7-Methylimidazo[1,2-a]pyrimidin-3-yl)phenyl]pyridine-2-carbonitrile수율 34.3%

실험 절차

7-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-imidazo[1,2-a]pyrimidine (0.1 g, 0.29 mmol) was coupled to 3-bromopyridine-2-carbonitrile (0.11 g, 0.59 mmol) as described in Example 24. The crude product was applied to two preparative plates (silica gel) and eluted with 5% methanol in dichloromethane. The appropriate band was collected and processed, affording a solid which was recrystallised from dichloromethane/ethyl acetate/isohexane to give 3-[3-(7-methylimidazo[1,2-a]pyrimidin-3-yl)phenyl]pyridine-2-carbonitrile as a white solid (31 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 6.80 (1H, d, J 7), 7.55 (1H, td, J 8 and 1), 7.63-7.73 (3H, m), 7.77 (1H, m), 7.86 (1H, s), 7.94 (1H, dd, J 8 and 1.6), 8.75 (1H, d, J 1.6), 8.80 (1H, d, J 7); m/z (ES+) 312 (M++H).

후처리

  1. washeluted with 5% methanol in dichloromethane
  2. customThe appropriate band was collected
  3. customaffording a solid which
  4. customwas recrystallised from dichloromethane/ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-1bfc2a0d537b4c449181245c2cf26020
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642229B2

연결된 노트

불러오는 중…