2-Methoxyphenylboronic acid → HCID 68662737, compound

HRID 1865699Notes

Reaction equation

HRID 1865699 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=N[CH:7]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.[CH2:31]1COCC1.C(#N)C>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:31][CH:7]=1)[N:8]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[N:9]=[C:10]2[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:21][CH3:20]

Participants

5

Reactant 3

HCID 27339582-Methoxyphenylboronic acidHCID 22177404Acetonitrile tetrahydrofuranHCID 579757462,2-Dimethyl-propionic acid 5-bromo-3-iodo-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

Product 1

HCID 68662737HCID 68662737, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 2,2-dimethyl-propionic acid 5-bromo-3-iodo-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (5 g, 11.4 mmol), 2-methoxy-phenyl boronic acid (1.7 g, 11.4 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (420 mg, 0.6 mmol) in THF/Acetonitrile/saturated NaHCO3 (10 ml/10 ml/15 ml) was stirred at 60° C. for 4 hours. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (3×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2,2-dimethyl-propionic acid 5-bromo-3-(2-methoxy-phenyl)-indazol-1-ylmethyl ester (3 g, 63% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.08 (s, 9H), 3.85 (s, 3H), 6.45 (s, 2H), 7.10 (m, 1H), 7.23 (d, 1H), 7.50 (m, 1H), 7.59 (d, 1H), 8.42 (s, 1H), 8.73 (s, 1H).

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with ethyl acetate (3×)
  3. extractionThe combined organic layers were extracted with brine
  4. dry with materialdried with Na2SO4
  5. customdecanted
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1efdfe5263864bbab0d931fbc4fa2f99
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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