Sodium Carbonate → N-(5-(2-fluorobenzyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473085Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH:23]([NH:27][S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])[CH2:22][CH2:21]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C(Cl)Cl.C1C(=O)[N-]C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd+]>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[CH:23]([NH:27][S:28]([CH:31]([CH3:33])[CH3:32])(=[O:29])=[O:30])[CH2:22][CH2:21]2

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-fluorobenzyl bromide (33 μL, 0.27 mmol), N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (100 mg, 0.27 mmol), trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) (11 mg, 0.014 mmol), and sodium carbonate (145 mg, 1.37 mmol) in degassed tetrahydrofuran (1.33 mL) and water (0.66 mL) was stirred at 80° C. for 16 h. The reaction was then diluted with 6 mL of DCM and 2 mL of water and the mixture was filtered over a phase separator. The organic phase was evaporated to dryness in vacuo to afford a brown oil in. Purification by silica flash column chromatography (EtOAc/heptane: from 0% to 60% of EtOAc) afforded the title compound as an oil (63.1 mg, 66%). MS (ESI): m/z [M−H]− 346.0

Workup

filtrationthe mixture was filtered over a phase separator
customThe organic phase was evaporated to dryness in vacuo
customto afford a brown oil in
customPurification by silica flash column chromatography (EtOAc/heptane: from 0% to 60% of EtOAc)

Sources & evidence

ORD record: ord-9625f7d211104f7fa37d4392de27f671
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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