1,1'-Carbonyldiimidazole → tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate

HRID 2108836ノート

反応式

HRID 2108836 の反応式
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[H][H].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1.[Pd]>[CH3:1][N:2]1[C:3]2[CH:4]=[C:5]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=2[NH:9][C:28]1=[O:29]

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86609347HCID 86609347、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 86609348tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate収率 77.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of tert-butyl [(3-methylamino-4-nitrophenyl)methyl]carbamate (864 mg, 3.07 mmol) and 10% Pd—C (100 mg) in THF was charged with hydrogen carefully. After stirring for 6 hours at room temperature, the reaction was recharged with nitrogen. Then, filtration, evaporation gave the residue, which was used for further reaction without purification. To the THF solution of the above, CDI (597 mg, 3.68 mmol) was added and the mixture was stirred for 4 hours at room temperature. After evaporation, purification through silica gel column chromatography eluting with CH2Cl2/MeOH (15:1) gave tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate as white solid (658 mg, 77%). 1H NMR (CDCl3): δ 1.47 (9H, s), 4.35 (2H, d, J=5.2 Hz), 4.92 (2H, brs), 6.86-7.10 (3H, m), 9.73 (1H, brs) MS (ESI) m/z 278 (M+H)+.

後処理

  1. filtrationThen, filtration, evaporation
  2. customgave the residue, which
  3. customwas used for further reaction without purification
  4. stirringthe mixture was stirred for 4 hours at room temperature
  5. customAfter evaporation, purification through silica gel column chromatography
  6. washeluting with CH2Cl2/MeOH (15:1)

出典と根拠

ORDレコード
ord-510fa389d8134ca0941a71e82adbc96e
出典データセット
uspto-grants-2009_04
特許番号
US07514457B2

反応ノート

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