Cesium carbonate → HCID 69482440, compound

HRID 2364245Notes

Reaction equation

HRID 2364245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:20][C:21](=O)[C:22](F)(F)F)[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ICC[CH2:36][S:37]([N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)(=[O:39])=[O:38]>CN(C)C=O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:20][CH2:21][CH2:22][CH2:36][S:37]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)(=[O:39])=[O:38])[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 69482047HCID 69482047, compound2×HCID 86612778HCID 86612778, compound

Product 1

HCID 69482440HCID 69482440, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-[(4-fluorophenyl)methyl]-3-[(trifluoroacetyl)amino]-2-pyridinecarboxylate (206 mg, 0.556 mmol) in N,N-dimethylformamide (2 mL) was added cesium carbonate (362 mg, 1.11 mmol) and 1-[(3-iodopropyl)sulfonyl]pyrrolidine (253 mg, 0.834 mmol), respectively. The reaction mixture was stirred at 80° C. for 5 hours, after which additional cesium carbonate (362 mg, 1.11 mmol) and 1-[(3-iodopropyl)sulfonyl]pyrrolidine (253 mg, 0.834 mmol) were added. The reaction mixture was stirred at 80° C. for an additional 7 hours. The reaction mixture was cooled and diluted with toluene. The resulting mixture was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5% gradient, methanol in dichloromethane) provided ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(1-pyrrolidinylsulfonyl)propyl]amino}-2-pyridinecarboxylate as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=1.3 Hz, 1 H), 7.79 (t, J=5.7 Hz, 1 H), 7.13 (dd, J=8.5, 5.4 Hz, 2 H), 6.97 (t, J=8.7 Hz, 2 H), 6.86 (s, 1 H), 4.41 (q, J=7.2 Hz, 2 H), 4.26 (t, J=6.2 Hz, 2 H), 3.91 (s, 2 H), 3.37-3.31 (m, 4 H), 3.03 (m, 2 H), 2.19-2.09 (m, 2 H), 1.95-1.89 (m, 4 H), 1.42 (t, J=6.9 Hz, 3 H); MS m/z 450 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for an additional 7 hours
  2. temperatureThe reaction mixture was cooled
  3. washThe resulting mixture was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9afe65dc2afb44529c81d40e7161a7c3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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