Potassium Carbonate → HCID 66580676, compound

HRID 1521868Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]2[S:8](=[O:30])(=[O:29])[CH2:9][C:10]3[C:14]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])=[N:13][N:12]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:11]=3[C:4]=2[CH:3]=1.[K+].[CH3:32][B-](F)(F)F.C([O-])([O-])=O.[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:32][C:2]1[CH:7]=[CH:6][C:5]2[S:8](=[O:29])(=[O:30])[CH2:9][C:10]3[C:14]([C:15]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)=[O:16])=[N:13][N:12]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:11]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

8-bromo-3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (160 mg, 0.32 mmol) is dissolved in 1,4-Dioxane:water (4:2) to which is added methyltrifluoroborate potassium salt (80 mg, 0.65 mmol) and K2CO3 (90 mg, 0.65 mmol). The reaction mixture is degassed for 5 min and is added S-phos (6.5 mg, 0.016 mmol) followed by palladium acetate (3.6 mg, 0.016 mmol). The reaction mixture is heated under microwave for 2 h at 120° C. After this time, the reaction mass is concentrated and purified by silica gel flash chromatography to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.90-7.88 (d, J=8.0 Hz, 1H), 7.64-7.62 (m, 3H), 7.54-7.52 (m, 2H), 7.43-6.55 (d, J=7.5 Hz, 1H), 6.55 (s, 1H), 4.85 (s, 2H), 3.94 (m, 2H), 3.66 (m, 4H), 3.62 (m, 2H), 2.11 (s, 3H). MS (ESI+): 424.0. HPLC (max plot) 91.94%; Rt 4.17 min.

Workup

customThe reaction mixture is degassed for 5 min
concentrationAfter this time, the reaction mass is concentrated
custompurified by silica gel flash chromatography

Sources & evidence

ORD record: ord-5219959a784544149bb99737f89cc1af
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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