Sodium Carbonate → HCID 45275672, compound

HRID 1622376Notes

Reaction equation

HRID 1622376 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[S:17]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18]1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(#N)C>[S:17]1[CH:21]=[CH:20][C:19]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)=[CH:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275672HCID 45275672, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (17 mg, 0.060 mmol), thiophene-3-boronic acid (9.2 mg, 0.072 mmol), tetrakis(triphenylphosphine)palladium(0) (3.5 mg, 5 mol %), 0.5 M sodium carbonate (0.17 mL, 0.084 mmol) and acetonitrile (1 mL) for 50 min. The crude product was purified by preparative tlc (CH2Cl2, MeOH, 10:1) to furnish the title compound as a white solid (13 mg, 76%), LC-MS (ESI, 3.5 min) Rt 1.12 min, m/z 288 (100%, [M+H]+); m/z (ESI) C15H18N3OS requires 288.1165 found [M+H]+ 288.1163.

Workup

  1. customfor 50 min
  2. customThe crude product was purified by preparative tlc (CH2Cl2, MeOH, 10:1)

Sources & evidence

ORD record
ord-e61366de24994c4ab71ff26d2dc87350
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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