Potassium Carbonate → HCID 86698793, compound

HRID 338458Notes

Reaction equation

HRID 338458 reaction equation
Br[C:2]1[C:10]([CH3:11])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:7]=2)[CH:3]=1.[F:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[C:2]1[C:10]([CH3:11])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:7]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15789384(2-Fluoro-4-methoxyphenyl)boronic acidHCID 866987925-Bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

Product 1

HCID 86698793HCID 86698793, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole (600 mg, 1.75 mmol), 2-fluoro-4-methoxyphenylboronic acid (320 mg, 1.88 mmol) and 2 N aqueous potassium carbonate solution (1.8 mL, 3.6 mmol) in 1,4-dioxane (7.2 mL) was purged with N2 three times, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (66.0 mg, 0.090 mmol) and subjected to microwave irradiation at 90° C. for 40 minutes. The reaction mixture was filtered through Celite, rinsed with EtOAc and concentrated in vacuo. The residue was purified by flash chromatography (0-33% EtOAc/heptane) to provide the title compound (657 mg, 92% yield) as a yellow solid. MS (ES+) 387.3 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.09 (s, 1H), 7.62 (s, 1H), 7.52 (s, 1H), 7.19 (t, J=8.54 Hz, 1H), 6.78 (dd, J=8.42, 2.56 Hz, 1H), 6.73 (dd, J=11.47, 2.44 Hz, 1H), 5.75 (s, 2H), 3.87 (s, 3H), 3.64-3.70 (m, 2H), 2.28 (s, 3H), 0.93-1.00 (m, 2H), 0.00 (s, 9H).

Workup

  1. customwas purged with N2 three times
  2. customirradiation at 90° C. for 40 minutes
  3. filtrationThe reaction mixture was filtered through Celite
  4. washrinsed with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-33% EtOAc/heptane)

Sources & evidence

ORD record
ord-be5e020742dd4ba58a5a802babf7b0d7
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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