1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester → tert-Butyl 3-(3-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)phenethoxy)propanoate

HRID 909945Notes

Reaction equation

HRID 909945 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].[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1>>[CH3:20][O:21][CH2:22][CH2:23][N:24]1[CH:28]=[C:27]([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:26]=[N:25]1

Participants

3

Reactant 2

HCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol esterHCID 67075913HCID 67075913, compound

Product 1

HCID 59290425tert-Butyl 3-(3-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)phenethoxy)propanoate

Procedure

The subtitled compound (834 mg) was prepared from tert-butyl 3-(3-bromophenethoxy)propanoate [Preparation 3, Step i)] and 1-(2-methoxyethyl)-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]+=319 (MultiMode+) 1H NMR (300 MHz, CDCl3) δ 7.78 (s, 1H), 7.72 (s, 1H), 7.37-7.22 (m, 3H), 7.07 (d, J=7.5 Hz, 1H), 4.32 (t, J=5.2 Hz, 2H), 3.78 (t, J=5.3 Hz, 2H), 3.70 (t, J=6.5 Hz, 2H), 3.68 (t, J=7.5 Hz, 2H), 3.35 (s, 3H), 2.89 (t, J=7.2 Hz, 2H), 2.49 (t, J=6.4 Hz, 2H), 1.47 (s, 9H)

Sources & evidence

ORD record
ord-3e94563047414de0aa3f00a5b317d719
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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