Sodium Carbonate → HCID 54530686, compound

HRID 1856704Notes

Reaction equation

HRID 1856704 reaction equation
[OH:1][C@H:2]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:23]1[CH:24]=[C:25]([C:29]#[N:30])[CH:26]=[N:27][CH:28]=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>[OH:1][C@H:2]([CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:23]2[CH:28]=[N:27][CH:26]=[C:25]([CH:24]=2)[C:29]#[N:30])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 7367935-BromonicotinonitrileHCID 54529270HCID 54529270, compound

Product 1

HCID 54530686HCID 54530686, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

Prepared according to the method described in Example 21b) from (2R)-4-(2-hydroxy-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 28a)), 5-bromopyridine-3-carbonitrile (0.19 g), 2M aqueous sodium carbonate (0.60 ml) and tetrakis(triphenylphosphine)palladium(0) (0.014 g) with heating at 90° C. for 4 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as an oil (0.10 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by normal-phase HPLC
  3. washeluting with a gradient of 0-10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-00928d4f00894f0b85e31e4357e60b51
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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