Potassium trimethylsilanolate → HCID 71666207, compound

HRID 929069Notes

Reaction equation

HRID 929069 reaction equation
[CH:1]1([S:4]([N:7]2[C:11]3=[CH:12][C:13]4[S:17][N:16]=[N:15][C:14]=4[C:18]([F:19])=[C:10]3[N:9]([C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])C2=O)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[F:19][C:18]1[C:14]2[N:15]=[N:16][S:17][C:13]=2[CH:12]=[C:11]([NH:7][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:5])=[O:6])[C:10]=1[NH:9][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 89705459HCID 89705459, compound

Product 1

HCID 71666207HCID 71666207, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(cyclopropylsulfonyl)-4-fluoro-5-(2-fluoro-4-iodophenyl)-5H-imidazo[4′,5′:4,5]benzo[1,2-d][1,2,3]thiadiazol-6(7H)-one (70 mg, 0.13 mmol) in THF (5 mL) was added potassium trimethylsilanolate (17 mg, 0.13 mmol). After stirring at room temperature for 1 h, the reaction was quenched with saturated NH4Cl (aq.). The aqueous layer was extracted with ethyl acetate (6 mL×2). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residual crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1, v/v) to give the corresponding product (40 mg, 60.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.86 (s, 1H), 8.37 (s, 1H), 7.73 (s, 1H), 7.60 (dd, 1H), 7.30 (dd, 1H), 6.45 (m, 1H), 2.77 (m, 1H), 1.01-0.99 (m, 2H), 0.89-0.86 (m, 2H). MS APCI (+) m/z: 508.7, [M+H].

Workup

  1. customthe reaction was quenched with saturated NH4Cl (aq.)
  2. extractionThe aqueous layer was extracted with ethyl acetate (6 mL×2)
  3. washThe combined organic phase was washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1

Sources & evidence

ORD record
ord-bdfdf16765ff471c908f4752bfc13472
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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