2,3-Difluorophenol → tert-Butyl 4-[(1S)-1-({[5-chloro-2-(2,3-difluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

HRID 1293298Notes

Reaction equation

HRID 1293298 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[OH:35]>>[Cl:26][C:5]1[CH:6]=[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])[C:2]([O:35][C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=2[F:27])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 808792,3-DifluorophenolHCID 57572256tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

Product 1

HCID 69418851tert-Butyl 4-[(1S)-1-({[5-chloro-2-(2,3-difluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Procedure

The title compound was prepared according to the procedure described in step 2 of Example 45 from tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate (step 1 of Example 45) and 2,3-difluorophenol: 1H-NMR (CDCl3) δ 8.54 (1H, d, J=2.7 Hz), 8.11 (1H, d, J=2.7 Hz), 7.98–7.92 (3H, m), 7.43–7.40 (2H, m), 7.23–7.07 (3H, m), 5.43–5.32 (1H, m), 1.61–1.56 (12H, m); MS (ESI) m/z 489 (M+H)+, 487 (M−H)−.

Sources & evidence

ORD record
ord-549402aaffe948d39678e6e50644831d
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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