Cesium carbonate → HCID 71087516, compound

HRID 927509Notes

Reaction equation

HRID 927509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](C)=[CH:9][C:8]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:7](Br)[N:6]=1)=[O:4].[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:7]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:18])[CH:24]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86674761HCID 86674761, compound

Product 1

HCID 71087516HCID 71087516, compoundYield 363.1%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 6-bromo-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid methyl ester (0.185 g, 0.65 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.15 g, 0.96 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II) dichloride methylene chloride complex (CAN 95464-05-4, 20 mg) and cesium carbonate (CAN 534-17-8, 0.63 g, 2 mmol) in DMF (10 mL) was stirred overnight at 80° C. under a nitrogen atmosphere. After filtration, the reaction mixture was poured into water (20 mL) and washed with ethyl acetate (2×20 mL). The organic layer was concentrated in vacuo to provide the title compound (0.75 g, 73%) as black oil which was used in the next step without further purification; MS (EI): m/e=318.1 [M+H]+.

Workup

  1. filtrationAfter filtration
  2. additionthe reaction mixture was poured into water (20 mL)
  3. washwashed with ethyl acetate (2×20 mL)
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-f9ed9d95e405479585a6388fa8a0b9cb
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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