Trimethyl borate → HCID 86700158, compound

HRID 879356Notes

Reaction equation

HRID 879356 reaction equation
Br[C:2]1[C:3](=[O:18])[N:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH3:17])[N:12]=[CH:11]3)[CH:5]=[CH:6][CH:7]=1.C[O:20][B:21](OC)[O:22]C.[Li]CCCC>C1COCC1>[CH3:17][N:13]1[C:14]2[C:10](=[CH:9][C:8]([N:4]3[CH:5]=[CH:6][CH:7]=[C:2]([B:21]([OH:22])[OH:20])[C:3]3=[O:18])=[CH:16][CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 86700159HCID 86700159, compoundHCID 178418339Butyllithium

Product 1

HCID 86700158HCID 86700158, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (−78° C.) solution of 3-bromo-1-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one (87 mg, 0.287 mmol) and trimethylborate (137 μL, 1.234 mmol) in anhydrous THF (5.0 mL) was added n-BuLi (2.5 M in hexane, 0.71 mL) for 10 min. Quenched the reaction by water and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C13H13BN3O3: 270.1; found: 270.2.

Workup

  1. customQuenched
  2. customthe reaction by water
  3. custompurified by reverse phase HPLC
  4. washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record
ord-2e9dfcc55b5f441098062ee78f2d1f8a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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