Cesium carbonate → 2-Chloro-N-(2-(pyrimidin-2-yl)phenyl)-5-(trifluoromethyl)pyridin-4-amine

HRID 1887682Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[C:14]2[N:13]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (142 mg, 0.46 mmol), 2-(pyrimidin-2-yl)aniline (78 mg, 0.46 mmol), Pd2(dba)3 (23 mg, 0.025 mmol), xantphos (23 mg, 0.040 mmol) and cesium carbonate (325 mg, 1.0 mmol) in dioxane (4.5 ml) was microwave heated in a Biotage Initiator microwave synthesizer at 130° C. for 30′. The solvent was removed and the residue was purified by preparative HPLC (0.1% TFA in water/acetonitrile gradient) to yield the title compound.

Workup

customThe solvent was removed
customthe residue was purified by preparative HPLC (0.1% TFA in water/acetonitrile gradient)

Sources & evidence

ORD record: ord-f6a1e131383f4ff08917440ab7399276
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501763B2

Reaction notes

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