Potassium Carbonate → HCID 66657744, compound

HRID 420929Notes

Reaction equation

HRID 420929 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Cl:15])=[CH:10][N:9]=1.C1OCCOCCOCCOCCOCCOC1.[CH2:34]([O:36][C:37]([C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([OH:48])[CH:46]=2)[N:41]([C:49]2[CH:54]=[CH:53][C:52]([O:55][C:56]([F:59])([F:58])[F:57])=[CH:51][CH:50]=2)[C:40]=1[CH2:60][C:61]([O:63][CH2:64][CH3:65])=[O:62])=[O:38])[CH3:35]>CCOC(C)=O.CN(C=O)C>[CH2:34]([O:36][C:37]([C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([O:48][C:8]3[CH:13]=[CH:12][C:11]([CH2:14][Cl:15])=[CH:10][N:9]=3)[CH:46]=2)[N:41]([C:49]2[CH:50]=[CH:51][C:52]([O:55][C:56]([F:59])([F:57])[F:58])=[CH:53][CH:54]=2)[C:40]=1[CH2:60][C:61]([O:63][CH2:64][CH3:65])=[O:62])=[O:38])[CH3:35]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 66657846HCID 66657846, compound

Product 1

HCID 66657744HCID 66657744, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (138 mg, 1.0 mmol), 2-chloro-5-chloromethylpyridine (32 mg, 0.2 mmol) and 18-crown-6 (5 mg) were added to a mixture of 2-ethoxycarbonylmethyl-5-hydroxy-1-(4-trifluoromethoxyphenyl)indole-3-carboxylic acid ethyl ester (90 mg, 0.2 mmol, see step (b) Example 9) and DMF (5 mL). The mixture was stirred for 48 h at 70° C., cooled, diluted with EtOAc, filtered through Celite®, concentrated and purified by chromatography. Yield 60 mg (520%).

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite®
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-f28ab9b55a8847df844fc01a301cf08a
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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