Sodium Carbonate → HCID 70223637, compound

HRID 473088Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:7][CH2:6]2.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.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+]>[Cl:19][C:20]1[CH:25]=[C:24]([CH:23]=[CH:22][CH:21]=1)[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (50 mg, 0.174 mmol), 3-chlorophenylboronic acid (54.3 mg, 0.347 mmol), trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) (7.04 mg, 8.69 μmol), and Sodium carbonate (36.8 mg, 0.347 mmol) in degassed Tetrahydrofuran (1 mL) and Water (1 mL) was stirred at 60° C. for 5 h. The Reaction mixture was then filtered and partitioned between H2O and EtOAc, the organic layer separated and evaporated in vacuo. Purification by flash chromatography (0-100% EtOAc in heptane) afforded the title compound as a colourless oil (43 mg, 68%). MS (ESI): m/z [M−H]− 362.0

Workup

filtrationThe Reaction mixture was then filtered
custompartitioned between H2O and EtOAc
customthe organic layer separated
customevaporated in vacuo
customPurification by flash chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record: ord-81f82ccde6314cf792b04f471a2acf18
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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