Dichloromethane → HCID 86666953, compound

HRID 511033Notes

Reaction equation

HRID 511033 reaction equation
[Cl:1][C:2]1[C:3]([F:30])=[C:4](I)[C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH3:9])[CH:7]=1.CC1(C)C(C)(C)OB([C:39]2[CH:40]=[CH:41][C:42]([C:45]#[N:46])=[N:43][CH:44]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(#N)C.O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:30])=[C:4]([C:39]2[CH:40]=[CH:41][C:42]([C:45]#[N:46])=[N:43][CH:44]=2)[C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH3:9])[CH:7]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 86666954HCID 86666954, compound

Product 1

HCID 86666953HCID 86666953, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A solution of N-[1-(5-chloro-2-ethoxy-4-fluoro-3-iodophenyl)ethyl]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (170 mg, 0.31 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile (86 mg, 0.37 mmol, Frontier Scientific, Cat. No. C1628), sodium carbonate (66 mg, 0.62 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-(H), complex with dichloromethane (1:1) (31 mg, 0.037 mmol) in acetonitrile (1.5 mL) and water (0.4 mL) was degassed with nitrogen for 10 min and stirred at 95° C. for 2 hours. The reaction mixture was diluted with EtOAc, washed with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, filtered and concentrated to a crude residue which was purified by flash column chromatography using EtOAc in hexanes (25%-100%) to give the desired product (81 mg, 50%). LCMS for C26H26ClFN7O2 (M+H)+: m/z=522.2. Found: 522.2.

Workup

  1. washwashed with saturated sodium bicarbonate, water, and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a crude residue which
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-4250f2b114924b33a596b7a61894a14f
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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