Trifluoroacetic acid → 5-(3-Chloro-4-methoxyphenyl)-3-(indolin-5-yl)-1,2,4-oxadiazole
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH:19]=[CH:18]4)[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1COCC1.C(C(O)=O)(F)(F)F>>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH2:19][CH2:18]4)[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
Procedure
To a solution of the product of Step E (0.11 g; 0.34 mmol) in 1M BH3 in THF (0.68 ml; 0.68 mmol) CF3CO2H (1 ml) was added drop wise at 0° C. with stirring. After the addition was completed (˜5 min) the reaction was quenched with H2O (0.5 ml) and the solvents were removed under reduced pressure. The residue was diluted to 15 ml with EtOAc and was washed with 1 M NaOH (2×2 ml), brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.11 g; 100%) as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 2.6 (broad s, 1H+H2O); 3.12 (tr, 2H, J=8.4 Hz); 3.66 (tr, 2H, J=8.4 Hz); 3.98 (s, 3H); 6.71 (d, 1H, J=8.1 Hz); 7.07 (d, 1H, J=8.7 Hz); 7.83-7.88 (m, 2H); 8.05 (dd, 1H, J=2, 8.7 Hz); 8.21 (d, 1H, J=2 Hz).
Workup
- additionAfter the addition
- custom(˜5 min)
- customwas quenched with H2O (0.5 ml)
- customthe solvents were removed under reduced pressure
- additionThe residue was diluted to 15 ml with EtOAc
- washwas washed with 1 M NaOH (2×2 ml), brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customThe filtrate was evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-e68633ca75c04579b3afa3018dcc3eae
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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