1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-Butyl 3-(3-(1,5-dimethyl-1H-pyrazol-4-yl)phenethoxy)propanoate

HRID 909947Notes

Reaction equation

HRID 909947 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][N:21]1[C:25]([CH3:26])=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]1>>[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([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:23]=[N:22]1

Participants

3

Reactant 2

HCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67075913HCID 67075913, compound

Product 1

HCID 59290441tert-Butyl 3-(3-(1,5-dimethyl-1H-pyrazol-4-yl)phenethoxy)propanoate

Procedure

The subtitled compound (804 mg) was prepared from tert-butyl 3-(3-bromophenethoxy)propanoate [Preparation 3, Step i)] and 1 1,5-dimethyl-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 (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.33-7.26 (m, 1H), 7.21-7.18 (m, 2H), 7.12 (d, 1H), 3.84 (s, 3H), 3.69 (q, 4H), 2.91 (t, 2H), 2.49 (t, 2H), 2.38 (s, 3H), 1.43 (s, 9H).

Sources & evidence

ORD record
ord-ad0903ee4e1d403ababc86120f7e0b37
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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