Sodium Carbonate → HCID 70244861, compound

HRID 380014Notes

Reaction equation

HRID 380014 reaction equation
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.[CH3:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=1Br)=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:28]2[CH:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:27]=2[NH:26][C:24](=[O:25])[CH3:23])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 7065694-Acetamido-3-bromobenzotrifluorideHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 70244861HCID 70244861, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 2-bromo-4-(trifluoromethyl)acetanilide (0.28 g), 2M aqueous sodium carbonate (0.57 ml) and tetrakis(triphenylphosphine)palladium (0) (0.014 g) in ethanol (5 ml) with heating at reflux for 2 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-5% ethanol in dichloromethane to give the title compound as a solid (0.16 g).

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 2 hours
  4. customAfter work up, the residue was purified by normal-phase HPLC
  5. washeluting with a gradient of 0-5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-f0c27ce0db564334bdf36832d27adf90
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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