Sodium Carbonate → HCID 57942704, compound

HRID 1438117Notes

Reaction equation

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

Participants

Conditions

Temperature: 95 °C

Procedure

To 21B (0.53 g, 2.0 mmol), 3A (0.51 g, 2.4 mmol) and sodium carbonate (4.0 mL, 2M, 8.0 mmol) in 1,2-dimethoxyethane (25 mL, flushed and degassed (3×) with nitrogen) was added Pd(PPh3)4 (0.23 g, 0.2 mmol) under nitrogen. The reaction was heated to 95° C. for 3 h. The catalyst was filtered over celite and washed with ethyl acetate. The organic layer was washed with water, brine and then dried over sodium sulfate. The solvent was removed and the crude residue was purified by flash column chromatography to give 0.58 g of product 21C (69% yield).

Workup

filtrationThe catalyst was filtered over celite
washwashed with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
customThe solvent was removed
customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-5ccc6b8f1dc84382aa7101ef13428019
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622585B2

Reaction notes

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