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2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59405022, compound

HRID 2387990
Notes
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Reaction equation

HRID 2387990 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:21])[NH:8][C:9]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.Br[C:23]1[C:24]([C:30]([F:33])([F:32])[F:31])=[N:25][CH:26]=[C:27]([Cl:29])[CH:28]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1.C(O)(C)(C)C>[Cl:29][C:27]1[CH:28]=[C:23]([NH:1][C:2]2[N:3]=[CH:4][C:5]3[CH2:6][C:7](=[O:21])[NH:8][C:9]4[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=4[C:11]=3[N:12]=2)[C:24]([C:30]([F:33])([F:31])[F:32])=[N:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 534174683-Bromo-5-chloro-2-(trifluoromethyl)pyridineHCID 59405023HCID 59405023, compound

Product 1

HCID 59405022HCID 59405022, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.42 g, 1.44 mmol), 3-bromo-5-chloro-2-(trifluoromethyl)pyridine (0.37 g, 1.44 mmol), Xphos (0.054 g, 0.115 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.052 g, 0.057 mmol) in a sealed microwave tube was evacuated and purged with argon 3 times. To the vial were added tert-butyl alcohol (5.3 mL) and 1.00 M of t-BuOK in tert-butyl alcohol (2.0 mL, 2.0 mol) via syringe. The mixture was allowed to stir to mix well, then was subjected to microwave irradiation at 150° C. for 1200 sec. The mixture was allowed to cool to rt and THF (6 mL) was added. The mixture was filtered and the solid was washed with THF. The organic solutions were combined and concentrated. The residue was purified by column chromatography to give 2-{[5-chloro-2-(trifluoromethyl)pyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.081 g, 12%) as a solid.

Workup

  1. customwas evacuated
  2. custompurged with argon 3 times
  3. additionto mix well
  4. customirradiation at 150° C. for 1200 sec
  5. filtrationThe mixture was filtered
  6. washthe solid was washed with THF
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-133e4c3f5852412898b29a4b36408ffa
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes