Sodium Carbonate → HCID 10203615, compound

HRID 381874Notes

Reaction equation

HRID 381874 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:25])[NH:10][N:11]=[C:12]([CH3:24])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[F:26][C:27]([F:31])([F:30])[CH2:28]I.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:26][C:27]([F:31])([F:30])[CH2:28][N:10]1[C:9](=[O:25])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:12]([CH3:24])=[N:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 10155312HCID 10155312, compound

Product 1

HCID 10203615HCID 10203615, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 63 (100 mg, 0.28 mmol) was dissolved in anhydrous DMF (3 mL) and treated with 1,1,1-trifluoro-2-iodoethane (27.5 mL, 280 mmol) in presence of anhydrous sodium carbonate (130 mg, 1.2 mmol) at 50-60° C. for 2 hours. The reaction mixture was partitioned between water and ethyl acetate to provide the desired compound as an amorphous solid (60 mg, 48%). 1HNMR (300 MHz, CDCl3) δ 2.10 (s, 3H), 3.10 (s, 3H), 4.85 (q, J=9 Hz, 2H), 6.90 (m, 2H), 7.10 (d, J=6 Hz, J=9 Hz, 2H), 7.25 (m, 2H), 7.95 (d, J=9 Hz, 2H),. MS (DCI/NH3) 458 (M+NH4)+. Anal. calc. for C20H16N2F4SO3: C, 54.54; H, 3.66; N, 6.36. Found: C, 54.41; H, 3.56; N, 6.35.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate

Sources & evidence

ORD record
ord-d51b418852a64a1190d46462fbf4b937
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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