Tolylboronic acid → HCID 86665658, compound

HRID 1399764Notes

Reaction equation

HRID 1399764 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([Cl:16])[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.B(O)(O)[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1.C(N(CC)C(C)C)(C)C>COCCOC.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>[Cl:16][C:6]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]=1

Participants

7

Reactant 3

HCID 79799Tolylboronic acidHCID 81531DiisopropylethylamineHCID 86665659HCID 86665659, compound

Product 1

HCID 86665658HCID 86665658, compound

Reagents, catalysts & solvents 3

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

Procedure

methyl 2-(4,6-dichloro-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (1 eq), p-tolylboronic acid (1 eq), tetrakis(triphenylphosphine)palladium(0) (0.1 eq) are placed in a reaction tube and dissolved in a mixture of degassed DME and water (3/1 v/v; 5 mL/mmol). N,N-Diisopropylethylamine (4 eq) is added, the tube is sealed and irradiated in a microwave oven at 130° C. for 30 min. The reaction mixture is partitioned between brine and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. Purification of the crude material is performed by flash chromatography on silica gel using a linear gradient of ethyl acetate in heptane.

Workup

  1. customthe tube is sealed
  2. customirradiated in a microwave oven at 130° C. for 30 min
  3. customThe reaction mixture is partitioned between brine and dichloromethane
  4. filtrationfiltered over a phase separator
  5. filtrationfilter (1PS)
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the crude material

Sources & evidence

ORD record
ord-c113f481cc2143feb78542e412e645c3
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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