Sodium Carbonate → HCID 45275877, compound

HRID 1622387Notes

Reaction equation

HRID 1622387 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.Cl.Cl.[CH3:20][N:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][N:24]=1)[CH3:22].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>[Cl:17][C:6]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)=[C:2]([C:26]2[CH:25]=[N:24][C:23]([N:21]([CH3:22])[CH3:20])=[CH:28][CH:27]=2)[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamideHCID 44118205[6-(Dimethylamino)pyridin-3-yl]boronic acid--hydrogen chloride (1/2)

Product 1

HCID 45275877HCID 45275877, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure E was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (50 mg, 0.18 mmol), 2-(N,N-dimethylamino)pyridine-5-boronic acid 2HCl salt (55 mg, 0.23 mmol), tetrakis(triphenylphosphine)palladium(0) (11 mg, 5 mol %), acetonitrile (2 mL) and 0.5 M sodium carbonate (1.3 mL, 0.66 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 25+S) followed by preparative tlc (CH2Cl2, MeOH, 9:1) to furnish the title compound as an off white solid (6 mg, 9%), LC-MS (ESI, 4 min) Rt 1.28 min, m/z 360 (100%, [M+H]+); m/z (ESI) C17H22N5OCl requires 359.1513, found [M+H]+ 359.1511.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 25+S)

Sources & evidence

ORD record
ord-b427c723741142ebb0c5764a48214c45
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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