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

HRID 1875452Notes

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

Participants

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

filtrationfiltered
concentrationconcentrated in vacuo
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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