HCID 59191571, compound → HCID 59191606, compound

HRID 1479979Notes

Reaction equation

HRID 1479979 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH3:9])=[CH:4][N:3]=1.C([Li])(C)(C)C.[CH2:25]([C:32]1[N:37]=[N:36][C:35]([N:38]2[CH2:43][CH2:42][C:41](=[O:44])[CH2:40][CH2:39]2)=[C:34]([CH3:45])[C:33]=1[CH3:46])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:25]([C:32]1[N:37]=[N:36][C:35]([N:38]2[CH2:39][CH2:40][C:41]([OH:44])([C:2]3[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH3:9])=[CH:4][N:3]=3)[CH2:42][CH2:43]2)=[C:34]([CH3:45])[C:33]=1[CH3:46])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 59191571HCID 59191571, compoundHCID 59191584HCID 59191584, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59191606HCID 59191606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To compound 34 (272 mg, 0.786 mmol) in THF (6 mL) at −78° C. is added t-butyl lithium (1.7 M in pentane, 1.0 mL, 1.7 mmol). The mixture is stirred at −78° C. for 30 min, to which compound 24 (209 mg, 0.707 mmol) in THF (2 mL) is added at −78° C. The mixture is stirred and warmed up slowly to −40° C. in 1 h, then quenched at −40° C. with saturated ammonium chloride. THF is removed and the residue was extracted with ethyl acetate (3×). The organic phase is washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue is purified by silica gel chromatography (40-60% ethyl acetate in heptane) to provide recovered compound 24 (103 mg, 49%) and the title compound 35 (106 mg, 27%) as a white solid.

Workup

  1. additionis added at −78° C
  2. customquenched at −40° C. with saturated ammonium chloride
  3. customTHF is removed
  4. extractionthe residue was extracted with ethyl acetate (3×)
  5. washThe organic phase is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel chromatography (40-60% ethyl acetate in heptane)
  9. customto provide
  10. customrecovered compound 24 (103 mg, 49%)

Sources & evidence

ORD record
ord-8298e22618f94e2f93f4c9eb0ca562b8
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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