HCID 86720518, compound → HCID 67509829, compound

HRID 1054095Notes

Reaction equation

HRID 1054095 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.[CH3:19][Mg]Br>>[C:1]1([C:11]2[N:12]=[CH:13][C:14]([CH:15]([OH:16])[CH3:19])=[CH:17][CH:18]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 86720518HCID 86720518, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67509829HCID 67509829, compound

Procedure

Synthesized using compound 54b (231 mg, 0.99 mmol) and methylmagnesium bromide (1.98 mL, 1.98 mmol, 1 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (2:1) as eluent. White solid. Yield: 172 mg, 70%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.59 (d, J=6.1 Hz, 3H), 5.00 (m, 1H), 7.44-7.62 (m, 5H), 7.80-7.86 (m, 1H), 7.90-7.96 (m, 2H), 8.07 (d, J=7.9 Hz, 1H), 8.74 (s, 1H); (ESI): m/z=250.29 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-77d5b051bbea40babd6b4bddbadf52ff
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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