Ammonium formate → (1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol

HRID 1880069ノート

反応式

HRID 1880069 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][O:28][CH2:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)[OH:11]

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 59327026(1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

生成物 1

HCID 59326884(1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A 350 ml heavy-walled vessel was charged with (1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone (1.2 g, 3.02 mmol) and ammonium formate (5.71 g, 91 mmol) in THF (20 mL) and MeOH (20.00 mL). The reaction was evacuated 2× and treated with palladium on carbon 10% (0.321 g, 0.302 mmol) under nitrogen. The vessel was capped and the mixture was heated to 70° C. After 6 hours, the reaction was allowed to cool down to RT and filtered through celite. The filtrate was reduced under vacuum and the resulting residue was partition with DCM and water. The DCM layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 2 to 12% MeOH in DCM to give (1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol as a white solid. MS (ESI, pos. ion) m/z: 401.9 (M+1).

後処理

  1. customThe reaction was evacuated 2×
  2. customThe vessel was capped
  3. temperatureto cool down to RT
  4. filtrationfiltered through celite
  5. customthe resulting residue was partition with DCM and water
  6. washThe DCM layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  7. dry with materialThe organic layer was then dried with sodium sulfate
  8. custompurified by column chromatography on silica gel using a gradient of 2 to 12% MeOH in DCM

出典と根拠

ORDレコード
ord-08fdd91383bc4ff38de9365e8adfdc6b
出典データセット
uspto-grants-2012_11
特許番号
US08318718B2

反応ノート

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