2-Bromopyridine → HCID 178522105, compound

HRID 2406804Notes

Reaction equation

HRID 2406804 reaction equation
[F:1][C:2]([F:28])([F:27])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][O:17][C:18]2[C:19]([C:24]([NH2:26])=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:10])[CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][N:79]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[N:79]1[CH:80]=[CH:81][CH:82]=[CH:83][C:78]=1[NH:26][C:24](=[O:25])[C:19]1[C:18]([O:17][CH2:16][C@H:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([C:2]([F:1])([F:27])[F:28])[CH2:4][CH2:5]2)=[O:10])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178513798HCID 178513798, compound

Product 1

HCID 178522105HCID 178522105, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of 3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinamide (30 mg, 0.08 mmol, EXAMPLE 75 Step 1), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (XANTPHOS) (3.47 mg, 6.00 micromol), cesium carbonate (0.10 g, 0.30 mmol), and tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (1.56 mg, 1.50 micromol) in 1,4-dioxane (2 mL) was added 2-bromopyridine (14 mg, 0.09 mmol) at room temperature. After being stirred at 120° C. for 12 h under microwave irradiation, water was added to the mixture. The mixture was extracted with ethyl acetate twice. The extracts were combined and dried over magnesium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by preparative HPLC.

Workup

  1. additionwas added to the mixture
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customThe residual oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-1916386edbbc4938bf0b3b3d09dd69e1
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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