Sodium Carbonate → HCID 68290686, compound

HRID 2205901Notes

Reaction equation

HRID 2205901 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:3]=1[NH2:4].I[C:19]1[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.CCOC(C)=O.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>[Cl:1][C:2]1[CH:8]=[C:7]([C:19]2[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 133340573-Iodo-1-methyl-1H-pyrazoleHCID 441187962-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 68290686HCID 68290686, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
135 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0.046 g, 0.039 mmol) was added to a solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.394 mmol), 3-iodo-1-methyl-1H-pyrazole (0.123 g, 0.592 mmol) and sodium carbonate (0.125 g, 1.183 mmol) in DME/H2O 3/1 (2.00 mL). The reaction mixture was heated for 1 hour at 135° C. under microwave irradiation before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a yellow solid (60 mg, 73%). 1H NMR (500 MHz, CDCl3): δ 3.93 (s, 3H), 4.09 (br s, 2H), 6.42 (d, J=2.3 Hz, 1H), 6.79 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.3 Hz, 1H), 7.50 (dd, J=8.3, 2.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 2.35 min, 208 [(M+H+), 100%].

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude mixture was purified via Biotage silica gel column chromatography
  8. washeluting with (Cyclohexane/EtOAc 80/20 to 60/40)

Sources & evidence

ORD record
ord-0c4084c43985405ea2c7a5aaeafb40e7
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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