4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide → N-(4-{1-[4-(2-Hydroxyethyl)phenyl]-3,5-dimethyl-1H-pyrazol-4-yl}phenyl)acetamide

HRID 891162Notes

Reaction equation

HRID 891162 reaction equation
I[C:2]1[C:3]([CH3:17])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].CC1(C)C(C)(C)OB([C:26]2[CH:35]=[CH:34][C:29]([NH:30][C:31](=[O:33])[CH3:32])=[CH:28][CH:27]=2)O1>>[OH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[C:6]([CH3:7])=[C:2]([C:26]3[CH:35]=[CH:34][C:29]([NH:30][C:31](=[O:33])[CH3:32])=[CH:28][CH:27]=3)[C:3]([CH3:17])=[N:4]2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 27346194'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilideHCID 222445592-[4-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

Product 1

HCID 22244633N-(4-{1-[4-(2-Hydroxyethyl)phenyl]-3,5-dimethyl-1H-pyrazol-4-yl}phenyl)acetamide

Procedure

The title compound was prepared according to the procedure described in step 1 of Example 12 from 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11) and 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide: MS (EI) m/z 385 [M]+, 1H-NMR (CDCl3) δ 7.44-7.26 (8H, m), 3.92-3.90 (2H, br), 3.08 (3H, s), 2.94 (2H, t, J=6.6 Hz), 2.32 (3H, s), 2.29 (3H, s).

Sources & evidence

ORD record
ord-0e995505be6b42c4912803b6406a11f4
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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