Sodium Hydroxide → HCID 117780519, compound

HRID 520328Notes

Reaction equation

[C:1]([C:5]1[CH:23]=[CH:22][C:8]2[N:9](C)[C:10]([C:12]3[C:17]([CH2:18][OH:19])=[C:16]([Cl:20])[CH:15]=[CH:14][N:13]=3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]([O:27][CH2:28][C:29]1[C:30]([C:36]2[N:40]([CH3:41])[C:39]3[CH:42]=[CH:43][C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:45][C:38]=3[N:37]=2)=[N:31][CH:32]=[CH:33][C:34]=1[Cl:35])(=O)C.[OH-].[Na+]>C(O)C.O>[C:1]([C:5]1[CH:23]=[CH:22][C:8]2[N:9]=[C:10]([C:12]3[C:17]([CH2:18][OH:19])=[C:16]([Cl:20])[CH:15]=[CH:14][N:13]=3)[N:11]([CH3:24])[C:7]=2[CH:6]=1)([CH3:2])([CH3:3])[CH3:4].[C:46]([C:44]1[CH:43]=[CH:42][C:39]2[N:40]([CH3:41])[C:36]([C:30]3[C:29]([CH2:28][OH:27])=[C:34]([Cl:35])[CH:33]=[CH:32][N:31]=3)=[N:37][C:38]=2[CH:45]=1)([CH3:49])([CH3:47])[CH3:48]

Participants

Conditions

Temperature: 19 °C

Procedure

A mixture of 160l and 160j (480 mg, 1.3 mmol), and sodium hydroxide (104 mg, 2.6 mmol) in ethanol (20 mL) and water (20 mL) was stirred at 19° C. for 2 h. See FIG. 5. The mixture was diluted with water (20 mL) and extracted with EtOAc (20 mL×2). The organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (2-(6-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methanol 160k and (2-(5-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methanol 160l as a mixture of regioisomers (400 mg, 94%). MS-ESI: [M+H]+ 330.2.

Workup

extractionextracted with EtOAc (20 mL×2)
washThe organic layers were washed with brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-065ff2aad4cc45e086147e43bb5c4a1c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326985B2

Reaction notes

Loading…