Dichloromethane → HCID 68027114, compound

HRID 527929Notes

Reaction equation

HRID 527929 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[N:17]=[CH:18][C:19]([C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)=[CH:20][CH:21]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 68027112HCID 68027112, compound

Product 1

HCID 68027114HCID 68027114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under N2, a mixture of (R)—N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-5-iodo-N-methylpyridin-2-amine (90.0 mg, 0.21 mmol), pyridin-4-yl boronic acid (28.4 mg, 0.23 mmol), PdCl2dppf.CH2Cl2 (17.2 mg, 0.02 mmol) and K2CO3 (0.058 g) in DMF (5.0 mL) was stirred at 110° C. for 16 h. It was then cooled to ambient temperature, diluted with water (5.0 mL) and extracted with ethyl acetate (3×10 mL). The combined extracts was washed with brine (3×5.0 mL), dried over Na2SO4 (anhydrous), filtered and concentrated. The residue was purified by flash chromatography to give the title product. MS (m/z): 372 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined extracts was washed with brine (3×5.0 mL)
  3. dry with materialdried over Na2SO4 (anhydrous)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7b0d2a0d117a4352be9b5b1f51b4e7f3
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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