Trifluoroacetic acid → HCID 67044243, compound

HRID 1944438Notes

Reaction equation

HRID 1944438 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH:13]=O)=[CH:3][CH:2]=1.[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH3:29].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.ClCCCl>[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[S:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[C:20]1[CH3:29]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 86652194HCID 86652194, compound

Product 1

HCID 67044243HCID 67044243, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(pyridin-4-ylsulfanyl)thiophene-2-carbaldehyde (1.3 g), (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (1.3 g) and 1,2-dichloroethane (30 mL) at −10° C. was treated with a mixture of triethylsilane (5.8 mL), trifluoroacetic acid (2.4 mL) and 1,2-dichloroethane (20 mL), and the resulting mixture was stirred at room temperature for 48 hours. The mixture was diluted with dichloromethane, washed with aqueous sodium bicarbonate solution and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to afford the title compound as yellow foam (2.4 g).

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c1a781dbaaf34f92a6b7e7a5c4a00fa5
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…