Water → HCID 51347934, compound

HRID 2370992Notes

Reaction equation

HRID 2370992 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:29])[O:4][N:3]=1.B(F)(F)F.S(C)C.O>C(Cl)Cl.CO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:29])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 6356Boron trifluorideHCID 67109704HCID 67109704, compound

Product 1

HCID 51347934HCID 51347934, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
1 °C

Procedure

2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-methoxyphenyl)-1H-indole-1-carboxamide (8 mg, 0.02 mmol) was dissolved in 8 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.40 ml) was added drop wise and the mixture was stirred at 0-2° C. for 16 h. A few drops MeOH were added followed by water. The layers were separated and the organic layer was concentrated. The crude product was purified by preparative HPLC. 3.4 mg 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide was obtained. ES/MS m/z: 376.1 (pos. M+H), 374.2 (neg. M−H); 1H NMR (acetone-d6, 500 MHz): 7.90 (m, 1H), 7.63 (m, 1H), 7.33 (m, 1H), 7.23 (m, 1H), 7.14 (m, 2H), 6.88 (m, 2H), 3.38 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H) and 1.16 (t, 3H, J=7.3 Hz).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe layers were separated
  3. concentrationthe organic layer was concentrated
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-82d829c6a5994c9d80e65ee8d346a2cf
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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