Sodium Carbonate → HCID 86730088, compound

HRID 880035Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[C:14]=2[O:21][CH3:22])=[O:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.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>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C@H:8]([NH:10][C:11]([C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[C:14]=3[O:21][CH3:22])=[O:12])[CH3:9])[CH:3]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)—N-(1-(3-bromophenyl)ethyl)-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide (Intermediate 12) (60 mg, 0.16 mmol) in DME (1.0 mL) was added 4-fluorophenylboronic acid (46.0 mg, 0.329 mmol), sodium carbonate (0.246 mL, 0.493 mmol), and tetrakis(triphenylphosphine)palladium(0) (38.0 mg, 0.0330 mmol) in a microwave vial. The reaction was degassed 3 times under argon and heated at 100° C. overnight. The reaction mixture was diluted with DCM and the organic portion dried over MgSO4, filtered and concentrated to give Example 47A which was used directly in the next step without further purification.

Workup

customThe reaction was degassed 3 times under argon
additionThe reaction mixture was diluted with DCM
dry with materialthe organic portion dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give Example 47A which
customwas used directly in the next step without further purification

Sources & evidence

ORD record: ord-ed5a6b8781514ac0a260bdc493272633
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993557B2

Reaction notes

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