Potassium trimethylsilanolate → HCID 71668125, compound

HRID 929031Notes

Reaction equation

HRID 929031 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:19]3[C:11](=[CH:12][C:13]4[S:17][CH:16]=[N:15][C:14]=4[C:18]=3[F:20])[N:10]([S:21]([CH:24]3[CH2:26][CH2:25]3)(=[O:23])=[O:22])C2=O)=[C:4]([Cl:28])[CH:3]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:19]2[C:11]([NH:10][S:21]([CH:24]3[CH2:25][CH2:26]3)(=[O:22])=[O:23])=[CH:12][C:13]3[S:17][CH:16]=[N:15][C:14]=3[C:18]=2[F:20])=[C:4]([Cl:28])[CH:3]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 89705349HCID 89705349, compound

Product 1

HCID 71668125HCID 71668125, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-bromo-2-chlorophenyl)-7-(cyclopropylsulfonyl)-4-fluoro-5H-imidazo[4′,5′:4,5]benzo[1,2-d]thiazol-6(7H)-one (50 mg, 0.10 mmol) in THF (5 mL) was added potassium trimethylsilanolate (13 mg, 0.10 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 (10 mL×2). The combined organic phase was washed with brine (20 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) and the product was obtained (30 mg, 63.3% yield). 1H NMR (400 MHz, CDCl3): δ 8.65 (s, 1H), 8.00 (s, 1H), 7.89 (d, 1H), 7.84 (s, 1H), 7.75 (d, 1H), 7.43 (m, 1H), 5.48 (s, 1H), 2.84 (m, 1H), 1.29 (m, 2H), 1.23 (m, 2H). MS APCI (+) m/z: 477.9, [M+H].

Workup

  1. customthe reaction was quenched with saturated NH4Cl (aq.)
  2. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
  3. washThe combined organic phase was washed with brine (20 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
  8. customv/v) and the product was obtained (30 mg, 63.3% yield)

Sources & evidence

ORD record
ord-99a6c8ebcfd148e6a13f78044c0ae179
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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