HCID 86720517, compound → HCID 67510676, compound

HRID 1054092Notes

Reaction equation

HRID 1054092 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][N:7]=2)=[CH:2]1.[CH:14]1([Mg]Br)[CH2:16][CH2:15]1>>[CH:14]1([CH:10]([C:9]2[CH:8]=[N:7][C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)=[CH:13][CH:12]=2)[OH:11])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 86720517HCID 86720517, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 67510676HCID 67510676, compound

Procedure

Synthesized using compound 47b (168 mg, 0.97 mmol) and cyclopropylmagnesium bromide (3.88 mL, 1.94 mmol, 0.5 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:1) as eluent. Yellow oil. Yield: 140 mg, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.35-0.44 (m, 1H), 0.49 (td, J=9.6, 5.0 Hz, 1H), 0.55-0.70 (m, 2H), 1.16-1.25 (m, 1H), 2.71 (br, s, 1H), 4.04 (d, J=8.2 Hz, 1H), 6.89 (dd, J=1.9, 0.6 Hz, 1H), 7.44 (dd, J=8.0, 0.8 Hz, 1H), 7.48-7.50 (m, 1H), 7.75-7.79 (m, 1H), 8.02 (dd, J=1.4, 0.8 Hz, 1H), 8.56 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=2.8, 3.6, 19.1, 76.0, 108.6, 119.8, 126.8, 134.4, 137.3, 141.1, 143.8, 147.6, 150.9; MS (ESI): m/z=216.27 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (3:1) as eluent

Sources & evidence

ORD record
ord-a760e6afc7f448ba8124ff82fd51878f
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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