tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate → tert-butyl 4-(5-chloro-4-fluoro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylate

HRID 46367Notes

Reaction equation

HRID 46367 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4](I)[CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH:20]=[N:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:23]=2)O1>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([C:19]2[CH:20]=[N:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:23]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 594365134-Chloro-5-fluoro-2-iodophenol

Product 1

HCID 59436628tert-butyl 4-(5-chloro-4-fluoro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylateYield 45%

Procedure

Prepared using the method of Example 587 using 4-chloro-5-fluoro-2-iodophenol (Preparation 744, 386 mg, 1.42 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (500 mg, 1.70 mmol) gave the title compound as a white solid (200 mg, 38%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bd073e59ccb64df08aa02581d6fe50ec
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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