3-Methyl-1H-pyrazole-4-boronic acid pinacol ester → HCID 59022982, compound

HRID 1924905Notes

Reaction equation

HRID 1924905 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:17]1[N:22]2[CH:23]=[CH:24][N:25]=[C:21]2[C:20]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[N:19][CH:18]=1>O1CCOCC1.CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:39][N:36]1[CH2:37][CH2:38][N:33]([C:30]2[CH:31]=[CH:32][C:27]([NH:26][C:20]3[C:21]4[N:22]([CH:23]=[CH:24][N:25]=4)[C:17]([C:3]4[CH:4]=[N:5][NH:6][C:2]=4[CH3:1])=[CH:18][N:19]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35]1

Participants

7

Reactant 2

HCID 177502703-Methyl-1H-pyrazole-4-boronic acid pinacol esterHCID 59022979(5-Bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine

Product 1

HCID 59022982HCID 59022982, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

In the same way as described for Compound 127, step 4, using 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (75 mg, 0.36 mmol), (5-bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine (70 mg, 0.18 mmol) and Pd(PPh3)4 (52 mg, 0.045 mmol) in dioxane (0.6 mL), DMF (1.33 mL) and 1.5M Na2CO3 (0.97 mL). The residue is chromatographed on silica gel, eluting with DCM followed by 95:5 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated. The title compound is isolated as a solid. HPLC (254 nm): Rt 1.62 min (98.2%); m/z (APCI) 389 (M+H)+.

Workup

  1. customThe residue is chromatographed on silica gel
  2. washeluting with DCM
  3. additionNH3 (7M in MeOH), and the fractions containing the desired product
  4. customevaporated

Sources & evidence

ORD record
ord-c2b3e50e37a24bacaf31b73ef3fbfd67
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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