Ethyl Acetate → HCID 67235382, compound

HRID 1261398Notes

Reaction equation

HRID 1261398 reaction equation
C[Si](C)(C)[O-].[K+].[CH2:7]([C:10]1([S:13]([N:16]2[C:20]3[C:21]4[O:25][CH:24]=[CH:23][C:22]=4[C:26]([F:29])=[C:27]([F:28])[C:19]=3[N:18]([C:30]3[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=3[F:37])C2=O)(=[O:15])=[O:14])[CH2:12][CH2:11]1)[CH:8]=[CH2:9].C(OCC)(=O)C>C1COCC1.CCCCCC>[CH2:7]([C:10]1([S:13]([NH:16][C:20]2[C:21]3[O:25][CH:24]=[CH:23][C:22]=3[C:26]([F:29])=[C:27]([F:28])[C:19]=2[NH:18][C:30]2[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=2[F:37])(=[O:15])=[O:14])[CH2:12][CH2:11]1)[CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 68313529HCID 68313529, compound

Product 1

HCID 67235382HCID 67235382, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

Potassium trimethyl silanolate (0.105 g, 0.82 mmol) was added to a solution of 1-(1-allylcyclopropylsulfonyl)-4,5-difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one (0.230 g, 0.4108 mmol) in THF (5 mL) at 0° C. The reaction mass was stirred for 4 hours at 20-40° C. The reaction was monitored by TLC (10% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure and the concentrate was extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford the crude compound. Purification by column chromatography on silica gel (10% ethyl acetate in hexane) afforded 0.177 g of the product (78% yield). 1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H), 7.40 (dd, 1H), 7.25 (s, 1H), 7.05 (bs, 1H), 6.99 (d, 1H), 6.32-6.39 (m, 1H), 6.22 (s, 1H), 5.65-5.75 (m, 1H), 5.19 (s, 1H), 5.10 (d, 1H), 2.88 (d, 2H), 1.15 (t, 2H), 0.75 (t, 2H). LCMS: 96.32%, m/z=548.8 (M+1). HPLC: 97.19%.

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. extractionthe concentrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude compound
  7. customPurification by column chromatography on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8792555b8a4747d78b262940cd25fc22
Source dataset
uspto-grants-2013_06
Patent number
US08470878B2

Reaction notes

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