Acetic Acid → HCID 11466590, compound

HRID 1296684Notes

Reaction equation

HRID 1296684 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:27][CH:26]=3)=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][C:4]=1[CH3:39].Br.CC(O)=O>CCOC(C)=O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:27][CH:26]=3)=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][C:4]=1[CH3:39]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 58913086HCID 58913086, compound

Product 1

HCID 11466590HCID 11466590, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-methoxy-6-methyl-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-3-(4-trifluoromethyl-phenyl)-chromen-2-one (50 mg, 0.093 mmol) in 1:1 48% HBr:AcOH (3 μL) was heated at 130° C. for 7 h. The mixture was cooled to room temperature and poured into AcOEt/1 M NaOH. The layers were separated and the organic phase was washed with H2O (2×) and brine and dried (MgSO4). The solvent was removed in vacuo. The residue was purified using reverse phase HPLC, followed by extraction with AcOEt/NaHCO3 to provide the desired compound as a yellow solid (25 mg, 52%). 1H NMR (300 MHz, CDCl3) δ 7.60 (d, J=8.0 Hz, 2H), 7.32 (d, J=8.0 Hz, 2H), 7.21 (d, J=0.75 Hz, 1H), 6.86 (d, J=8.8 Hz, 2H), 6.72 (s, 1H), 6.62 (d, J=8.8 Hz, 2H), 4.14 (t, J=5.5 Hz, 2H), 3.92 (s, 2H), 3.13 (t, J=5.5 Hz, 2H), 2.97–2.85 (br s, 4H), 2.13 (s, 3H), 2.00–1.89 (m, 4H); MS (ESI) m/z 523.9 (M)+; HPLC tR 5.07 min.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with H2O (2×) and brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified
  6. extractionfollowed by extraction with AcOEt/NaHCO3

Sources & evidence

ORD record
ord-96e788a5041b44d2a9e4b1765f698f6c
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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