Sodium Carbonate → HCID 67036357, compound

HRID 473390Notes

Reaction equation

HRID 473390 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([F:19])=[C:14](B(O)O)[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.O.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>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([F:19])=[C:14]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochlorideHCID 53375375HCID 53375375, compound

Product 1

HCID 67036357HCID 67036357, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of compound 11 (135 mg, 0.5 mmol), 4-chloropyridine hydrochloride (107 mg, 0.713 mmol), tetrakis(triphenylphosphine)palladium (45 mg, 0.04 mmol) and Na2CO3 (160 mg, 1.51 mmol) in dimethoxyethane (2.2 mL) and water (0.7 mL) mixture, is heated to 85° C. for 5 h. The mixture is cooled to rt and partitioned between water and EtOAc. The organic phase is dried using Na2SO4 and concentrated on rotary evaporator to afford 100 mg (59%) of compound 13. 1H NMR (300 MHz, CDCl3) δ 8.68-8.62 (m, 2H), 7.80-7.42 (m, 2H), 7.40-7.35 (m, 1H), 7.36-7.24 (m, 1H), 7.18-7.08 (m, 1H), 5.26-5.18 (br s, 1H), 4.25 (d, J=5.5 Hz, 2H), 1.44 (s, 9H).

Workup

  1. temperatureThe mixture is cooled to rt
  2. custompartitioned between water and EtOAc
  3. customThe organic phase is dried
  4. concentrationconcentrated on rotary evaporator

Sources & evidence

ORD record
ord-d63989f843094400872e6e6a7137b0d4
Source dataset
uspto-grants-2014_01
Patent number
US08633321B2

Reaction notes

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