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Sodium Carbonate → HCID 21830744, compound

HRID 1600929
Notes
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Reaction equation

HRID 1600929 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][CH:25]([O:37][Si](C(C)(C)C)(C)C)[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=2)[CH:18]=1.F>C(#N)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.C(O)C.C1(C)C=CC=CC=1>[OH:37][CH:25]([CH2:24][CH2:23][C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:8]2[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([NH2:13])=[O:12])[CH:9]=2)=[CH:30][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 898073-BromobenzamideHCID 21717159HCID 21717159, compound

Product 1

HCID 21830744HCID 21830744, compoundYield 24.8%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 1.4 ml), ethanol (0.8 ml), 3-bromobenzamide (0.5 g), (±)-4-[4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butoxy]benzeneboronic acid (1.0 g) and tetrakis(triphenylphosphine)palladium(0) (70 mg) with heating at 120° C. for 3 hours. The residue obtained after work up was purified by column chromatography over silica eluting with 5% ethanol in dichloromethane to give a yellow gum which was deprotected as in Example 34e) using hydrofluoric acid (40%, 5 ml, CAUTION) in acetonitrile (20 ml). The residue obtained after work up was triturated with diethyl ether to give the title compound as a pale yellow solid (0.224 g)

Workup

  1. customPrepared
  2. customThe residue obtained after work
  3. customup was purified by column chromatography over silica eluting with 5% ethanol in dichloromethane
  4. customto give a yellow gum which
  5. customThe residue obtained after work
  6. customup was triturated with diethyl ether

Sources & evidence

ORD record
ord-977b5a6a1a1a4e30b4a45dee4bfce37d
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977105

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes