Sodium hydride → 1-({2-tert-Butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1435533Notes

Reaction equation

HRID 1435533 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4]1.[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][CH:23]([F:26])[CH2:22][CH2:21]2)[C:17]2[CH:27]=[CH:28][C:29]([S:31](Cl)(=[O:33])=[O:32])=[CH:30][C:16]=2[N:15]=1)([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:21][CH2:22][CH:23]([F:26])[CH2:24][CH2:25]2)[C:17]2[CH:27]=[CH:28][C:29]([S:31]([N:3]3[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4]3)(=[O:32])=[O:33])=[CH:30][C:16]=2[N:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehydeHCID 57937318HCID 57937318, compound

Product 1

HCID 579373941-({2-tert-Butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrrole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.19 g, 60%, 4.8 mmol) was added to a solution of 1H-pyrrole-3-carbaldehyde (0.13 g, 1.4 mmol) in THF (30 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature, stirred for 1 h and cooled to 0° C. 2-tert-Butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (0.37 g, 0.96 mmol) was added to the reaction mixture and stirred for 1 h. The reaction mixture was quenched with saturated NaHCO3 solution (30 mL) and the solvent was concentrated. Water (50 mL) was added to the residue and the product was extracted with DCM (workup). The solvent was concentrated and the product was purified by MPLC on silica gel using 50-80% EtOAc/heptane to provide the title compound as white solid. Yield: 0.25 g (57%); MS (ESI) (M+H)+=445.9.

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred for 1 h
  3. customThe reaction mixture was quenched with saturated NaHCO3 solution (30 mL)
  4. concentrationthe solvent was concentrated
  5. additionWater (50 mL) was added to the residue
  6. extractionthe product was extracted with DCM (workup)
  7. concentrationThe solvent was concentrated
  8. customthe product was purified by MPLC on silica gel using 50-80% EtOAc/heptane

Sources & evidence

ORD record
ord-9f5be5495a9346d7979571633bb5f414
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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