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1,2-Dichloroethane → 7-Fluoro-indole-5-carboxylic acid (n-[2-hydroxy-2-(3,4,5-trimethoxyphenyl) ethyl]) amide

HRID 1976784
Notes
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Reaction equation

HRID 1976784 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Cl.[NH2:15][CH2:16][CH:17]([C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)[OH:18].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[OH:18][CH:17]([C:19]1[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=1)[CH2:16][NH:15][C:11]([C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][CH:8]=[CH:7]2)=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 115645587-Fluoro-1H-indole-5-carboxylic acidHCID 24194781BENZYL ALCOHOL, alpha-(AMINOMETHYL)-3,4,5-TRIMETHOXY-, HYDROCHLORIDE

Product 1

HCID 544358387-Fluoro-indole-5-carboxylic acid (n-[2-hydroxy-2-(3,4,5-trimethoxyphenyl) ethyl]) amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 63D in DMF (10 mL)was treated sequentially with 2-amino-1-(3,4,5-trimethoxyphenyl)ethanol hydrochloric acid salt (0.343 g, 1.30 mmol), EDC (0.325 g, 1.7 mmol), triethylamine, DMAP (catalytic), heated at 50° C. for 15 hours, cooled to room temperature, poured into water (100 ml), and extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 8:2 ethyl acetate/hexanes to provide 0.24 g of the desired product.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography on silica gel with 8:2 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-87196e0cf78149cca35fdcb4ef36457b
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06228868B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes