Sodium Carbonate → {6-Methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,3,4,9-tetrahydro-beta-carbolin-2-yl}-phenyl-acetic acid ethyl ester

HRID 563919Notes

Reaction equation

HRID 563919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[NH:9][CH2:8][CH2:7][C:6]2=1.Br[CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH2:33]([O:32][C:30](=[O:31])[CH:29]([N:9]1[CH2:8][CH2:7][C:6]2[C:5]3[C:13](=[CH:14][CH:15]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:12][C:11]=2[CH:10]1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 97780Ethyl bromophenylacetateHCID 598200086-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 59819991{6-Methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,3,4,9-tetrahydro-beta-carbolin-2-yl}-phenyl-acetic acid ethyl esterYield 16.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 90 mg (0.24 mmol) 6-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-2,3,4,9-tetrahydro-1H-β-carboline, 59 mg (0.24 mmol) ethyl bromophenylacetate and 28.8 mg (0.27 mmol) Na2CO3 in 4 mL methanol was heated to reflux for 16 h. After filtration DMF was added and the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The combined product fractions were evaporated to dryness to yield 21 mg (16%) {6-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,3,4,9-tetrahydro-β-carbolin-2-yl}-phenyl-acetic acid ethyl ester (diastereoisomer 1)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. filtrationAfter filtration DMF
  4. additionwas added
  5. customthe mixture was subjected to purification by preparative HPLC on reversed phase
  6. washeluting with a gradient
  7. customformed from acetonitrile, water and formic acid
  8. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-f6b8080bd1c84d1f8469005f49e4d55e
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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