Hydrochloric Acid → HCID 66919817, compound

HRID 1971720Notes

Reaction equation

HRID 1971720 reaction equation
Br[C:2]1[C:3]([O:32][CH3:33])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:26])[N:16]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:13]=4[C:12]([C:27]4[S:31][CH:30]=[N:29][CH:28]=4)=[C:9]3[C:10]=2[CH:11]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>C(Cl)Cl.C(OCC)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.O.C(COC)OC>[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:2]2[C:3]([O:32][CH3:33])=[CH:4][C:5]3[CH2:6][CH2:7][N:8]4[C:14]5[C:15](=[O:26])[N:16]([C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:13]=5[C:12]([C:27]5[S:31][CH:30]=[N:29][CH:28]=5)=[C:9]4[C:10]=3[CH:11]=2)[CH:35]=1

Participants

11

Reactant 5

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27343783-Pyridinylboronic acidHCID 66919875HCID 66919875, compound

Product 1

HCID 66919817HCID 66919817, compoundYield 100.3%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 12 mg of 16m, 6 mg of pyridine-3-boronic acid, 10 mg of K2CO3, 1.5 ml of degassed dimethoxyethane, 100 μl of water and 5 mg of Pd(PPh3)4 was heated at 90° C. for 4 hr under a N2 atmosphere. The mixture was cooled and poured into 10 ml of 2N NaOH and extracted with ethyl acetate. The extract was washed once with water, dried and chromatographed using a gradient of heptane/acetone as eluent. The material thus isolated was taken up in 200 μl of CH2Cl2 and treated with 0.2N HCl in diethyl ether, to pH slight acidic, to provide 12 mg of 16n as a yellowish HCl salt, MS-ESI:

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed once with water
  4. customdried
  5. customchromatographed
  6. customThe material thus isolated

Sources & evidence

ORD record
ord-f861ded2cf1d47cc9386c0b22bb9e025
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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