Cesium carbonate → HCID 59618055, compound

HRID 449893Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:19])[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[CH:5]=[CH:4][N:3]=1.[N:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[N:22][CH:21]=1.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+]>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].O1CCOCC1>[Cl:18][C:11]1[CH:12]=[C:13]([Cl:17])[CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:23]2[CH:24]=[CH:25][N:20]=[CH:21][N:22]=2)[CH:7]=1)=[O:19]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-(2-bromopyridin-4-yl)-2,4,6-trichlorobenzamide (76 mg, 0.20 mmol), pyrimidin-4-amine (38 mg, 0.40 mmol), Pd2(dba)3 (18.3 mg, 0.020 mmol), Xantphos (23.3 mg, 0.040 mmol), Cs2CO3 (131 mg, 0.40 mmol), and dioxane (1.2 mL) was heated at 140° C. for 1 hour in a microwave reactor under nitrogen atmosphere. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford the desired product (46.5 mg, yield: 59%). 1H NMR (500 MHz, MeOH-d4): δ 8.68 (s, 1H), 8.36 (d, J=6.0 Hz, 1H), 8.26 (d, J=6.0 Hz, 1H), 8.19 (s, 1H), 7.71 (d, J=6.0 Hz, 1H), 7.65 (s, 2H), 7.35 (m, 1H). LCMS (ESI) m/z: 394.0 [M+H+].

Workup

filtrationThe mixture was filtered through Celite
concentrationconcentrated under reduced pressure
customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record: ord-2a8acd50f0714076aa9f7031d35ffb5d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

Loading…