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Sodium Hydroxide → HCID 86651544, compound

HRID 1809472
Notes
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Reaction equation

HRID 1809472 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](=[N:34][NH2:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(O)C(C)C.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:35][N:34]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 79304DiphenylmethylidenehydrazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 69809311HCID 69809311, compound

Product 1

HCID 86651544HCID 86651544, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 6560IsobutanolSolvent

Procedure

A mixture of (F1), benzophenone hydrazone (1.8 eq.), ground NaOH (1.4 eq.), Pd(AcO)2 (0.05 eq.) and XPhos (0.1 eq.) in degassed iBuOH (0.18 M) was stirred under argon at RT for 20 min and then was heated at 80° C. for 3 h. After cooling down, evaporation of the solvent gave a residue that was dissolved in DCM and washed with sat. aq. NH4Cl (2×) and sat. aq. NaHCO3 (2×) and dried (Na2SO4). Evaporation of the solvent gave a crude that was purified by flash chromatography column on silica (EtOAc/Petroleum ether 2:98 to 1:4) yielding (90%) the title compound as a yellow foam. 1H NMR (300 MHz, DMSO-d6, 300K) δ 8.68 (1H, s), 7.67-7.49 (3H, m), 7.46-7.39 (2H, m), 7.37-7.25 (10H, m), 7.13 (2H, d, J=8.3 Hz), 7.04 (2H, d, J=8.3 Hz), 3.47 (2H, s), 2.92-2.75 (2H, m), 2.70-2.56 (1H, m), 2.06-1.86 (2H, m), 1.83-1.50 (3H, m), 1.48-1.32 (1H, m). MS (ES+) C31H31N3 required: 445, found: 446 (M+H)+.

Workup

  1. temperaturewas heated at 80° C. for 3 h
  2. temperatureAfter cooling down
  3. customevaporation of the solvent
  4. customgave a residue that
  5. washwashed with sat. aq. NH4Cl (2×) and sat. aq. NaHCO3 (2×)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave a crude that
  9. customwas purified by flash chromatography column on silica (EtOAc/Petroleum ether 2:98 to 1:4)

Sources & evidence

ORD record
ord-9ce1864ae3e4421099ae871124fa4121
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362030B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes