Sodium Bicarbonate → HCID 54471613, compound

HRID 1479821Notes

Reaction equation

Cl.Br[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16]([C:3]2[CH:4]=[C:5]([CH2:6][NH2:7])[CH:8]=[CH:9][CH:10]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 3-bromobenzylamine hydrochloride 22 (1 g, 4.49 mmol) in DME (50 mL) was added with 4-trifluoromethyl phenyl boronic acid (1.2 mol eq, 1.0 g) and NaHCO3 (3 mol eq, 1.13 g) suspended in water (30 mL). The mixture was degassed under vacuum, then Tetrakispalladium was added (catalytic amount) and the reaction was stirred at 100° C. under inert atmosphere for 12 h. The solvent was removed under reduced pressure and water was added to the residue (80 mL). The aqueous phase was extracted with EtOAc (3×40 mL) and the combined organic layer was washed with brine (50 mL) and dried over Na2SO4. The solvent was evaporated under vacuum to afford 23A as a pale brown oil (1.5 g, quantitative yield).

Workup

customThe mixture was degassed under vacuum
additionTetrakispalladium was added (catalytic amount)
customThe solvent was removed under reduced pressure and water
additionwas added to the residue (80 mL)
extractionThe aqueous phase was extracted with EtOAc (3×40 mL)
washthe combined organic layer was washed with brine (50 mL)
dry with materialdried over Na2SO4
customThe solvent was evaporated under vacuum

Sources & evidence

ORD record: ord-178098a9e89446a3996922f435585e41
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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