Sodium Carbonate → HCID 45275350, compound

HRID 1622358Notes

Reaction equation

HRID 1622358 reaction equation
Br[C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:10]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:8][C:5]1[N:4]=[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:10]2)[C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 45275249HCID 45275249, compound

Product 1

HCID 45275350HCID 45275350, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-(5-bromo-2-chloropyrimidin-4-yl)piperidine-4-carboxamide E31 (0.10 g, 0.31 mmol), benzene boronic acid (46 mg, 0.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 5 mol %) in DME (8 mL) was added a 0.5 M solution of sodium carbonate. The mixture was heated at relfux for 22 h, then cooled to r.t. and purified on an SCX-2 cartridge (MeOH, followed by 0.5 M NH3 in MeOH). The crude product was purified by chromatography on silica gel (CH2Cl2, MeOH, 98:2) to furnish the title compound as a white solid (58 mg, 59%), m/z 317 (100%, MH+); m/z (ESI) C16H18BrClN4O requires 317.1165 found [M+H]+ 317.1161.

Workup

  1. temperatureThe mixture was heated at relfux for 22 h
  2. custompurified on an SCX-2 cartridge (MeOH, followed by 0.5 M NH3 in MeOH)
  3. customThe crude product was purified by chromatography on silica gel (CH2Cl2, MeOH, 98:2)

Sources & evidence

ORD record
ord-67c93680ab874daea9c729cd2fa3c949
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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