Potassium Phosphate, Tribasic → 2-(3-(2-fluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole

HRID 634126Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.I[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]3[S:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[N:30][N:31]=3)[CH:25]=2)[N:20]([S:36]([C:39]2[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(N)CC1C=CC=CC=1.OP(O)(O)=O>CC(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]3[S:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[N:30][N:31]=3)[CH:25]=2)[N:20]([S:36]([C:39]2[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-(2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.639 g, 2.88 mmol), 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (1.150 g, 2.056 mmol) in 70% IPA/H2O (18 mL) was added potassium phosphate (1.309 g, 6.17 mmol), and AmPhos (0.073 g, 0.103 mmol). The reaction was heated at 100° C. for 5 min. The aq. layer was removed and the organic layer was evaporated. The residue was purified with prep HPLC to give 2-(3-(2-fluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (0.487 g, 0.923 mmol, 44.9%) as a light brown solid. MS (ESI, pos. ion) m/z: 528 (M+1).

Workup

customThe aq. layer was removed
customthe organic layer was evaporated
customThe residue was purified with prep HPLC

Sources & evidence

ORD record: ord-d72190f2ec744735aa9a2783876907b4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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