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

HRID 1976784Notes

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]

Participants

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

temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
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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