Iodoethane → HCID 68786219, compound

HRID 1632103Notes

Reaction equation

HRID 1632103 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][N:24]4[CH2:28][CH2:27][NH:26][C:25]4=[O:29])=[N:21][CH:22]=3)[C:9]=2[F:30])[CH:5]=[CH:6][CH:7]=1.[CH2:31]1COC[CH2:32]1.[H-].[Na+].C(I)C>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][N:24]4[CH2:28][CH2:27][N:26]([CH2:31][CH3:32])[C:25]4=[O:29])=[N:21][CH:22]=3)[C:9]=2[F:30])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 57703766HCID 57703766, compound

Product 1

HCID 68786219HCID 68786219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Into an 18 mL vial was added P-374 (65 mg, 0.16 mmol), THF (3 mL), and the solution was cooled to 0° C. NaH (9 mg, 0.23 mmol) was added and the suspension was stirred at room temperature for 15 minutes. EtI (25 uL, 0.31 mmol) was added and the reaction was stirred for 1 hour at room temperature. Water was added and the product was extracted with EtOAc (3×3 mL). The organics were washed with water, brine, and concentrated. To the residue was added 2 mL of 4N HCl/dioxane. After stirring to dissolve, the solution was concentrated. The resulting residue was triturated with ether, filtered, washed with ether, and dried to give P-461 (51 mg, 65%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) 8.63 (br s, 2H), 8.07 (br s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.50-7.33 (m, 4H), 7.29 (d, J=5.8 Hz, 1H), 6.97 (d, J=8.3 Hz, 1H), 4.51 (s, 2H), 4.09 (br s, 2H), 3.74 (s, 3H), 3.57 (s, 2H), 3.31 (s, 2H), 3.19-3.10 (m, 2H), 1.10-0.97 (m, 3H) ppm. LC/MS=84.2%, 454.2 (APCI+).

Workup

  1. stirringthe reaction was stirred for 1 hour at room temperature
  2. extractionthe product was extracted with EtOAc (3×3 mL)
  3. washThe organics were washed with water, brine
  4. concentrationconcentrated
  5. additionTo the residue was added 2 mL of 4N HCl/dioxane
  6. stirringAfter stirring
  7. dissolutionto dissolve
  8. concentrationthe solution was concentrated
  9. customThe resulting residue was triturated with ether
  10. filtrationfiltered
  11. washwashed with ether
  12. customdried
  13. customto give P-461 (51 mg, 65%) as a tan solid

Sources & evidence

ORD record
ord-437a977b67544a73bb322f49c043981e
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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