Tetrabutylammonium Fluoride → 3-[-1-(2-fluorophenyl)ethoxy]-5-[6-(hydroxymethyl)-3H-imidazo[4,5-c]pyridin-3-yl]thiophene-2-carboxamide

HRID 2391661Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]([C:19]3[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([O:27][CH:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[F:36])[CH3:29])[CH:20]=3)[CH:17]=[N:18][C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH:28]([O:27][C:21]1[CH:20]=[C:19]([N:16]2[C:13]3[CH:14]=[N:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[N:18]=[CH:17]2)[S:23][C:22]=1[C:24]([NH2:26])=[O:25])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4.44 g of 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-[1-(2-fluorophenyl)ethoxy]thiophene-2-carboxamide in 300 ml THF is cooled to 0° C. At 0° C. 2.31 ml tetra-n-butylammonium fluoride (˜75% in H20) are added. The reaction mixture is allowed to warm to room temperature and stirred over night.

Workup

customAt 0° C
temperatureto warm to room temperature

Sources & evidence

ORD record: ord-78d193a1a2834c9c8a8ecd8a305cc451
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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