1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester → tert-Butyl 3-(3-(1-ethyl-1H-pyrazol-4-yl)phenethoxy)propanoate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH2:20]([N:22]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[N:23]1)[CH3:21]>>[CH2:20]([N:22]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=2)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:24]=[N:23]1)[CH3:21]Participants
3
Procedure
The subtitled compound (0.64 g) was prepared from tert-butyl 3-(3-bromophenethoxy)propanoate [Preparation 3, Step i)] and 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole using a similar method to that described in Example 18, Step i). MS[M+H-C4H8]+=289 (MultiMode+) 1H NMR (300 MHz, CDCl3) δ 7.76 (s, 1H), 7.65 (s, 1H), 7.35-7.23 (m, 3H), 7.07 (d, J=7.5 Hz, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.70 (t, J=6.4 Hz, 2H), 3.68 (t, J=7.3 Hz, 2H), 2.89 (t, J=7.1 Hz, 2H), 2.49 (t, J=6.5 Hz, 2H), 1.53 (t, J=7.3 Hz, 3H), 1.43 (s, 9H)
Sources & evidence
- ORD record
- ord-2e1c02c12580474ab2f29213b55de161
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017602B2
Reaction notes
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