Water → tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate

HRID 634149Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17](B4OC(C)(C)C(C)(C)O4)[CH:18]=3)[N:13]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:12]=2)[CH:2]=1.Br[C:37]1[S:38][C:39]([S:42][CH3:43])=[N:40][N:41]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:43][S:42][C:39]1[S:38][C:37]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH:12]=[C:11]3[C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[N:41][N:40]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 3-(quinolin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (80 mg, 170 μmol), 2-bromo-5-(methylthio)-1,3,4-thiadiazole (54 mg, 255 μmol), Pd(PPh3)4 (9.8 mg, 8.5 μmol) and potassium carbonate (71 mg, 510 μmol) in dioxane (1.0 mL) was added H2O (0.2 mL). The reaction was heated in a microwave at 120° C. for 70 min. The solvent was then removed and the residue was purified with silica gel chromatography to give tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate (41 mg, 51%). MS (ESI, pos. ion) m/z: 475 (M+1).

Workup

customThe solvent was then removed
customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record: ord-44dfd6647e334421a2dc8f1c53229a8a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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