Sodium Carbonate → HCID 58464952, compound

HRID 1185409Notes

Reaction equation

HRID 1185409 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].CC1(C)C(C)(C)OB([C:19]2[CH2:24][CH2:23][CH2:22][CH:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:20]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[K+]>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].C(#N)C>[CH3:7][N:6]1[C:2]([C:19]2[CH2:24][CH2:23][CH2:22][CH:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:20]=2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 57812344HCID 57812344, compound

Product 1

HCID 58464952HCID 58464952, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

5-Chloro-1-methyl-4-nitropyrazole (100 mg, 0.62 mmol), tert-butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-yl]carbamate (240 mg, 0.74 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (45 mg, 0.061 mmol), a 1M solution of Na2CO3 (0.93 mL), a 1M solution of potassium acetate (0.93 mL) and acetonitrile (6 mL) were charged in a microwave reaction vial, The mixture was irradiated to 140° C. with a microwave for 30 min and cooled to room temperature. It was filtered through Celite and thoroughly washed with methanol. The filtrate was concentrated and the residue was purified via flash chromatography, 0 to 100% ethyl acetate in heptane to give tert-butyl N-[3-(2-methyl-4-nitro-pyrazol-3-yl)cyclohex-2-en-1-yl]carbamate (98 mg, 49%)

Workup

  1. customThe mixture was irradiated to 140° C. with a microwave for 30 min
  2. filtrationIt was filtered through Celite
  3. washthoroughly washed with methanol
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified via flash chromatography, 0 to 100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-ab18fa7a59284e8f99ba77c5c11687da
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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