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Potassium Carbonate → HCID 58124874, compound

HRID 1971681
Notes
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Reaction equation

HRID 1971681 reaction equation
Br[C:2]1[C:3]([O:37][CH3:38])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:31])[N:16]([CH:28]([CH3:30])[CH3:29])[CH2:17][CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][C:13]=4[C:12]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[C:9]3[C:10]=2[CH:11]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41](B(O)O)[CH:40]=1.C([O-])([O-])=O.[K+].[K+]>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.COCCOC>[CH:28]([N:16]1[C:15](=[O:31])[C:14]2[N:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:37][CH3:38])[C:2]([C:41]5[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=5)=[CH:11][C:10]=4[C:9]3=[C:12]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:13]=2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH2:17]1)([CH3:30])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 27343783-Pyridinylboronic acidHCID 58124866HCID 58124866, compound

Product 1

HCID 58124874HCID 58124874, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 60 mg of 10l, 22 mg of 3-pyridylboronic acid, 12 mg of Pd(PPh3)4 and 40 mg of K2CO3 in 3 ml of degassed 90% aq. DME was heated under N2 for 16 h. The reaction mixture was poured onto 1M K2CO3 solution and the product was extracted with ethyl acetate. The organic extract was washed once with sat. NaCl, dried and concentrated. The crude material thus obtained was chromatographed over silica gel, using heptane/acetone in a gradient. The isolated product was triturated with diethyl ether, to give 56 mg of 10m, Mp: 207-208° C.

Workup

  1. temperaturewas heated under N2 for 16 h
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed once with sat. NaCl
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material thus obtained
  8. customwas chromatographed over silica gel
  9. customThe isolated product was triturated with diethyl ether

Sources & evidence

ORD record
ord-587ad52c644b420b9827c6f1461f39fc
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431564B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes