Sodium Bicarbonate → HCID 17984895, compound

HRID 1968682Notes

Reaction equation

HRID 1968682 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][C:3]=1[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].B1([C:26]2[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=2)OCCCO1.C([O-])(O)=O.[Na+]>COCCOC.CCOC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:4][C:3]=1[C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 17984899(2-Amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone

Product 1

HCID 17984895HCID 17984895, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (2-amino-5-bromo-3-nitro-phenyl)-cyclohexyl-methanone (600 mg, 1.83 mmol) in DME (25 mL) was added, successively, pyridine-3-boronic acid 1,3-propanediol cyclic ester (388 mg, 2.38 mmol), (tetrakistriphenylphosphine) palladium(0) (212 mg, 0.18 mmol), and 1N NaHCO3 (3.7 mL, 3.7 mmol). The resulting mixture was stirred at 90° C. for 90 minutes then cooled to room temperature. The reaction mixture was diluted with EtOAc (100 mL), washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and the filtrate concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc) to afford 527 mg (89%) of the title compound as a pale orange solid: 1H NMR (CDCl3, 500 MHz) δ 8.92 (d, 1H), 8.69 (d, 1H), 8.66 (d, 1H), 8.31 (d, 1H), 8.20 (d, 1H), 7.71 (dd, 1H), 3.36 (m, 1H), 1.88 (m, 3H), 1.77 (m, 1H), 1.40-1.61 (m, 3H), 1.24-1.32 (m, 2H), 0.89 (m, 1H).

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography (SiO2, hexanes to 3:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-84a8863183a0495999311564722d8e43
Source dataset
uspto-grants-2013_04
Patent number
US08426426B2

Reaction notes

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