HCID 86720518, compound → HCID 67510910, compound

HRID 1054094Notes

Reaction equation

HRID 1054094 reaction equation
[C:1]1([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:19]1([Mg]Br)[CH2:21][CH2:20]1>>[CH:19]1([CH:15]([C:14]2[CH:13]=[N:12][C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[CH:18][CH:17]=2)[OH:16])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 86720518HCID 86720518, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 67510910HCID 67510910, compound

Procedure

Synthesized using compound 54b (253 mg, 1.09 mmol) and cyclopropylmagnesium bromide (4.34 mL, 2.17 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. Light yellow solid. Yield: 239 mg, 80%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.39-0.54 (m, 2H), 0.60-0.72 (m, 2H), 1.22-1.29 (m, 1H), 4.04-4.14 (m, 1H), 7.42-7.60 (m, 5H), 7.86-7.92 (m, 3H), 8.04-8.08 (m, 1H), 8.77 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=3.3, 3.9, 14.4, 60.6, 125.0, 125.5, 125.9, 126.1, 126.7, 127.7, 128.6, 129.1, 134.2, 137.8, 138.5, 147.8, 158.5, 171.4; MS (ESI): m/z=276.34 [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-1de0687bb18c464797cee4e615f0f50e
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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