Sodium ethoxide → HCID 66779074, compound

HRID 1470359Notes

Reaction equation

HRID 1470359 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11](I)=[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]5[CH:31]=[C:32]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)[O:33][C:26]=45)=[CH:20][CH:19]=3)=[O:16])[C:9]2=[O:40])=[CH:4][CH:3]=1.[O-:41][CH2:42][CH3:43].[Na+]>>[C:34]1([C:32]2[O:33][C:26]3[C:27](=[N:28][CH:29]=[CH:30][C:25]=3[O:24][C:21]3[CH:22]=[CH:23][C:18]([NH:17][C:15]([C:10]4[C:9](=[O:40])[N:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)[CH:13]=[CH:12][C:11]=4[O:41][CH2:42][CH3:43])=[O:16])=[CH:19][CH:20]=3)[CH:31]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 66779149HCID 66779149, compound

Product 1

HCID 66779074HCID 66779074, compoundYield 101.8%

Procedure

To a dry 5 mL sealed tube with stirbar was added 1-(4-fluorophenyl)-4-iodo-2-oxo-N-{4-[(2-phenylfuro[3,2-b]pyridin-7-yl)oxy]phenyl}-1,2-dihydropyridine-3-carboxamide (46.30 mg; 0.07 mmol; 1.00 eq.) and the vial was sealed and flushed with N2. To the vial was added dry THF (1.00 ml) via syringe and then sodium ethoxide (0.04 ml; 0.09 mmol; 1.30 eq.) (21% solution in ethanol) was slowly added via syringe and the reaction mixture was stirred at room temperature for 1 h. The solution was concentrated, taken up in EtOAc and washed with sat. aq. NaHCO3. The organic layer was collected, extracting aqueous layer with EtOAc (3×). Combined organic layers were dried (Na2SO4) and concentrated on rotary evaporator to afford the title compound as a beige solid (40 mg, 100%). (HPLC (method F): 99%, RT: 6.08 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.41 (s, 1H), 8.34 (d, J=5.5, 1H), 7.97-7.90 (m, 2H), 7.86 (d, J=7.8, 1H), 7.83-7.77 (m, 2H), 7.69 (s, 1H), 7.58-7.50 (m, 2H), 7.50-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.34-7.27 (m, 2H), 6.71 (d, J=5.5, 1H), 6.52 (d, J=7.9, 1H), 4.26 (q, J=7.0, 2H), 1.30 (t, J=7.0, 3H); MS (m/z) 562 [M+H]+, RT: 3.5 min.

Workup

  1. customTo a dry 5 mL sealed tube with stirbar
  2. customthe vial was sealed
  3. customflushed with N2
  4. additionTo the vial was added dry THF (1.00 ml) via syringe
  5. concentrationThe solution was concentrated
  6. washwashed with sat. aq. NaHCO3
  7. customThe organic layer was collected
  8. extractionextracting aqueous layer with EtOAc (3×)
  9. dry with materialCombined organic layers were dried (Na2SO4)
  10. concentrationconcentrated on rotary evaporator

Sources & evidence

ORD record
ord-72173d2526fb45ad92db31b35761f6b4
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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