tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate → HCID 89442459, compound

HRID 2284022Notes

Reaction equation

HRID 2284022 reaction equation
[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:9]=[C:8]2[CH:23]2[CH2:28][CH2:27][N:26]([C:29]3[N:34]=[CH:33][N:32]=[C:31]([NH2:35])[C:30]=3Br)[CH2:25][CH2:24]2)[CH2:4][CH2:3][CH2:2]1.C(OC([N:44]1[CH:48]=[C:47](B2OC(C)(C)C(C)(C)O2)[CH:46]=[N:45]1)=O)(C)(C)C>>[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:9]=[C:8]2[CH:23]2[CH2:28][CH2:27][N:26]([C:29]3[N:34]=[CH:33][N:32]=[C:31]([NH2:35])[C:30]=3[C:47]3[CH:48]=[N:44][NH:45][CH:46]=3)[CH2:25][CH2:24]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 89442950HCID 89442950, compound

Product 1

HCID 89442459HCID 89442459, compoundYield 15%

Conditions

Temperature
50 °C

Procedure

A mixture of 6-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-bromo-pyrimidin-4-ylamine (100.00 mg; 0.18 mmol; 1.00 eq.), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (77.63 mg; 0.26 mmol; 1.50 eq.), and in dioxane 2 ml and water 0.15 ml was degas, added Pd(t-Bu3)2 13 mg, stirred at 50° C. for overnight. Added methanol 5 ml, 4.0M HCl in dioxane 5 ml, stirred at RT for 4 hr, removed off solvent and purified by prep HPLC, collected title compound 15 mg, yield 12.7%. LC-MS: (M+1=556, obsd.=556).

Workup

  1. customin dioxane 2 ml and water 0.15 ml was degas
  2. additionadded Pd(t-Bu3)2 13 mg
  3. stirringAdded methanol 5 ml, 4.0M HCl in dioxane 5 ml, stirred at RT for 4 hr
  4. customremoved off solvent
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-2a51e562cb604789b2f11106b09fea73
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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