Sodium hydride → 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehyde

HRID 1435470Notes

Reaction equation

HRID 1435470 reaction equation
[CH3:1][C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22](Cl)(=[O:24])=[O:23])=[CH:21][C:8]=2[N:7]=1)([CH3:5])[CH2:3][CH3:4].[NH:26]1[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27]1.[H-].[Na+]>C1COCC1>[CH3:1][C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22]([N:26]3[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27]3)(=[O:24])=[O:23])=[CH:21][C:8]=2[N:7]=1)([CH3:5])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehydeHCID 579373072-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazole-5-sulfonyl chloride

Product 1

HCID 579373651-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehydeYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 29, using 2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (0.66 g, 1.7 mmol), 1H-pyrrole-3-carbaldehyde (0.14 g, 1.4 mmol) and sodium hydride (0.29 g, 60%, 7.2 mmol) in THF (15 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.45 g (71%) of a white solid as the title compound. MS (ESI) (M+H)+=443.93

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-05e03fcb79b74becae45522945b05e91
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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