Trifluoroacetic acid → ethyl (3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

HRID 2178369Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24]CC4C=CC(OC)=CC=4)=[C:20]([O:34][CH3:35])[CH:19]=3)[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:8]2[C:5]3=[N:6][CH:7]=[C:2]([I:1])[CH:3]=[C:4]3[N:10]=[C:9]2[NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:19][C:20]=1[O:34][CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl (6-iodo-3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (Example 3-34-2) (2.40 g, 4.08 mmol) in dichloromethane (50 mL) at 0° C. was added trifluoroacetic acid (4.47 g, 3.0 mL, 39.18 mmol). The resulting mixture was allowed to stir at 0° C. After 2 h, the mixture was treated with 2M potassium carbonate solution to adjust the pH to ˜9. The basic mixture was extracted with 1:1 methanol/dichloromethane solution (3×50 mL). The combined organic phases were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated to provide 1.30 g (70%) of ethyl (3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a light yellow solid.

Workup

extractionThe basic mixture was extracted with 1:1 methanol/dichloromethane solution (3×50 mL)
washThe combined organic phases were washed with brine (50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-76b88aaa9fc84bcab4e7b4f595054542
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067914B1

Reaction notes

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