Ammonium formate → (4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine

HRID 475231노트

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HRID 475231 반응식
[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=[N:18]O.C([O-])=O.[NH4+]>CO.[Zn]>[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:17][NH2:18]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 866947334-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

생성물 1

HCID 86694734(4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine수율 47.4%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

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온도
75 °C

실험 절차

To a solution of 150 (5.8 g, 0.022 mol) in MeOH (100 mL) was added zinc dust (2.9 g, 0.044 mol) and ammonium formate (2.8 g, 0.044 mol). The resulting mixture was heated to 75° C. for 2 h. The mixture was filtered through a Celite® pad. The filtrate was concentrated and the crude product was purified by SiO2 chromatography eluting with 5% MeOH/DCM to afford 2.6 g (47%) of (4-fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (152) as a yellow solid: 1H-NMR (400 MHz, RT, CDCl3): δ 1.66-1.80 (m, 3H), 1.92-1.96 (m, 1H), 2.06-2.14 (m, 2H), 3.68-3.74 (m, 1H), 4.23-4.26 (m, 1H), 4.40 (br, 2H), 5.49-5.52 (dd, 1H), 6.94-6.99 (dd, 1H), 7.18-7.23 (t, 1H), and 7.37-7.39 (d, 1H); MS (ESI) m/z=250.2 [M+1]+.

후처리

  1. filtrationThe mixture was filtered through a Celite® pad
  2. concentrationThe filtrate was concentrated
  3. customthe crude product was purified by SiO2 chromatography
  4. washeluting with 5% MeOH/DCM

출처 및 근거

ORD 기록
ord-7cc31387f4a1417bb5ceb9d19b2ef9da
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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