Sodium Carbonate → HCID 178509617, compound

HRID 1486483

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:35][N:36](C)C(=O)C>O.[Cl-].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+6]>[C:35]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH2:15][CH2:14]1)#[N:36]

Participants

Conditions

Temperature: 120 °C

Procedure

N-{trans-4-[(8-Bromoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide (500 mg, 1.13 mmol) (see example 12), sodium carbonate (120 mg, 1.13 mmol) and palladium(II) acetate (13 mg, 0.06 mmol) were dissolved in N,N-dimethylacetamide (23 mL) and finely triturated potassium hexacyanoferrate (105 mg, 2.5 mmol) was added. The reaction mixture was stirred under a nitrogen atmosphere for 3 hours at 120° C. After cooling to room temperature, the reaction mixture was diluted with water and saturated sodium chloride solution and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, then the sodium sulphate and solvent residues were removed. After chromatography of the residue, the desired product was obtained at 43% yield (190 mg).

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulphate
customthe sodium sulphate and solvent residues were removed

Sources & evidence

ORD record: ord-cd7c415faf06465e9aaab6efe123a5b2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428460B2

Linked notes

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