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

HRID 2108836Notes

Reaction equation

HRID 2108836 reaction equation
[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]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86609347HCID 86609347, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-510fa389d8134ca0941a71e82adbc96e
Source dataset
uspto-grants-2009_04
Patent number
US07514457B2

Reaction notes

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