Perchloric Acid → HCID 89462821, compound

HRID 1473262Notes

Reaction equation

HRID 1473262 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3[C:16]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)=[C:17]([CH:22]([OH:27])[C:23]([O:25][CH3:26])=[O:24])[N:18]([CH3:21])[C:19](=[O:20])[C:8]2=3)=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C.C(OCC)(=O)C>[C:5]([O:27][CH:22]([C:17]1[N:18]([CH3:21])[C:19](=[O:20])[C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:36][CH:35]=3)[C:15]3[C:10]([C:9]=2[C:16]=1[C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:23]([O:25][CH3:26])=[O:24])([CH3:35])([CH3:6])[CH3:4]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 89463080HCID 89463080, compound

Product 1

HCID 89462821HCID 89462821, compoundYield 126.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10908tert-Butyl acetateSolvent

Procedure

A solution of methyl 2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)-2-hydroxyacetate (42 mg, 0.087 mmol) in t-Butyl acetate (1 mL) was treated with perchloric acid (6.22 μL, 0.103 mmol) and then stirred at room temperature for 1 hour. The mixture was diluted with Ethyl acetate, washed with NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford methyl 2-(tert-butoxy)-2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)acetate as a white solid (30 mg, 0.055 mmol, 64% yield). 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.25-7.47 (m, 8H) 6.88-7.00 (m, 3H) 6.57-6.63 (m, 1H) 6.19-6.22 (m, 1H) 6.11-6.17 (m, 1H) 5.29 (s, 1H) 3.79 (s, 3H) 3.78 (s, 3H) 2.54 (s, 3H) 1.04 (s, 9H); LCMS (m/z) ES+=541 (M+1).

Workup

  1. washwashed with NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8e6cdaee5d30441f8825b442b9995f88
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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