Cesium carbonate → HCID 59127091, compound

HRID 1989990Notes

Reaction equation

HRID 1989990 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([O:7]C)=[O:6].[N:16]1([C:20]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][N:23]=2)=[O:21])[CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Br>[N:16]1([C:20]([C:22]2[N:23]=[CH:24][C:25]([O:1][C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=3)[C:5]([OH:7])=[O:6])=[CH:26][CH:27]=2)=[O:21])[CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoateHCID 536296172-(Azetidin-1-ylcarbonyl)-5-bromopyridine

Product 1

HCID 59127091HCID 59127091, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 11251615Bromotris(triphenylphosphine)copper(I)CatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of methyl 3-hydroxy-5-[(1-methylethyl)oxy]benzoate (0.84 g, 4 mmol), 2-(azetidin-1-ylcarbonyl)-5-bromopyridine (1.16 g, 4.8 mmol), cesium carbonate (3.92 g, 1.2 mmol) and bromotris(triphenylphosphine)copper(I) (744 mg, 0.8 mmol) in DMA (20 mL) was stirred in a microwave reactor at 160° C. for 6 hours. The mixture was diluted with water (100 mL), washed with ethyl acetate (2×20 mL) and the aqueous layer filtered then acidified with 2N hydrochloric acid. The acidic layer was extracted with ethyl acetate (3×50 mL), the combined organics washed with water (2×20 mL), brine (20 mL), dried (MgSO4), and the solvent removed in vacuo. The residue was triturated with ether to give the desired compound as a white solid (1.06 g). 1H NMR δ (d6-DMSO): 1.28 (d, 6H), 2.28 (quin, 2H), 4.08 (t, 2H), 4.59 (t, 2H), 4.69 (quin, 1H), 6.98 (t, 1H), 7.10 (s, 1H), 7.28 (s, 1H), 7.56 (d, 1H), 7.99 (d, 1H), 8.41 (s, 1H); m/z 357 (M+H)+

Workup

  1. washwashed with ethyl acetate (2×20 mL)
  2. filtrationthe aqueous layer filtered
  3. extractionThe acidic layer was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organics washed with water (2×20 mL), brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-ced9e0a3b6b745c3b16e5179a8174f9b
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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