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Cesium carbonate → 6-(3-(2-fluorobenzyl)-1H-indazol-1-yl)-1,3,5-triazine-2,4-diamine

HRID 1875452
Notes
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Reaction equation

HRID 1875452 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1.Cl[C:19]1[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.CO.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].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:19]2[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=2)[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178505618HCID 178505618, compound

Product 1

HCID 247944776-(3-(2-fluorobenzyl)-1H-indazol-1-yl)-1,3,5-triazine-2,4-diamine

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 887MethanolSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Under argon, 130 mg (0.58 mmol) of 3-(2-fluorobenzyl)-1H-indazole from example 5A, 84 mg (0.58 mmol) of 6-chloro-1,3,5-triazine-2,4-diamine, 11 mg (0.011 mmol) of tris(dibenzylidene-acetone)dipalladium, 16 mg (0.034 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 262 mg (0.80 mmol) of cesium carbonate are introduced into 4 ml of degassed toluene and heated at 90° C. for 20 h. The mixture is then diluted with ethyl acetate and methanol, filtered and concentrated in vacuo. The residue is purified by preparative HPLC to result in 36 mg (19% of theory) of the title compound. In addition, 65 mg of the starting compound are recovered.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-31846d97e9444bd99fcad11442b94617
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309551B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes