Toluene → HCID 58946487, compound

HRID 1038110Notes

Reaction equation

HRID 1038110 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17](B3OCC(C)(C)CO3)=[C:16]([F:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:30]1[N:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:30]3[N:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=3)=[C:16]([F:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 57686054HCID 57686054, compound

Product 1

HCID 58946487HCID 58946487, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

4-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-3-fluoro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (19AB)(1.55 g, 3.98 mmol, 1 equiv), 2-Chloro-5-fluoro-pyrimidine (20AB)(634 mg, 591 uL, 4.78 mmol, 1.2 equiv), and 2M sodium carbonate (9.95 mL) were added in a pressure vessel (350 mL) and a (1v:1v) mixture of toluene and ethanol (25 mL: 25 mL) was added. The mixture was then bubbled with nitrogen gas for about 10 minutes. Tetrakis(triphenylphosphine) palladium (0) (462 mg, 0.4 mmol, 0.1 equiv) was added to the mixture. The reaction vessel was tightly capped, placed in an oil bath at 90° C., and stirred overnight.

Workup

  1. additionwas added
  2. customThe mixture was then bubbled with nitrogen gas for about 10 minutes
  3. customThe reaction vessel was tightly capped
  4. customplaced in an oil bath at 90° C.

Sources & evidence

ORD record
ord-bf93cccc214d4e92a38985af068ea675
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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