Sodium hydride → 2-fluoro-4-(1-(2-methoxyethyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzonitrile

HRID 75523Notes

Reaction equation

[CH3:1][C:2]1[C:19]([CH3:20])=[CH:18][C:5]2[NH:6][C:7]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([F:17])[CH:10]=3)=[N:8][C:4]=2[CH:3]=1.Br[CH2:22][CH2:23][O:24][CH3:25].[H-].[Na+]>CN(C)C=O>[F:17][C:11]1[CH:10]=[C:9]([C:7]2[N:6]([CH2:22][CH2:23][O:24][CH3:25])[C:5]3[CH:18]=[C:19]([CH3:20])[C:2]([CH3:1])=[CH:3][C:4]=3[N:8]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-fluorobenzonitrile 3 (110 mg, 0.4 mmol) was combined with 1-bromo-2-methoxyethane (76 mg, 0.55 mmol), NaH (13 mg, 0.55 mmol), and N,N-dimethyl formamide (5 ml). The reaction was heated at 100° C. for 1.5 hours. The product solution (confirmed by LCMS: 324.22) was carried on to the next step without purification.

Workup

customThe product solution (confirmed by LCMS: 324.22) was carried on to the next step without purification

Sources & evidence

ORD record: ord-da32c225f4e44151be06823cb2e8b605
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835445B2

Reaction notes

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