Cesium carbonate → HCID 58958591, compound

HRID 915581Notes

Reaction equation

[CH:1]1([C:6]2[CH:10]=[C:9]([NH2:11])[N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[CH:1]1([C:6]2[CH:10]=[C:9]([NH:11][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([O:24][CH3:25])=[O:23])[N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate B, 400 mg, 1.66 mmol), methyl 2-bromobenzoate (297 mg, 1.38 mmol), cesium carbonate (630 mg, 1.93 mmol), BINAP (87 mg, 0.14 mmol), and Pd2(dba)3 (72 mg, 0.07 mmol) in anhydrous toluene (4 mL) was heated to 110° C. for 16 h under an argon atmosphere. The reaction mixture was cooled to rt, diluted with ethyl acetate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using EtOAc/Hex (1:8, v/v) as the eluent. The product was obtained as a light yellow oil (303 mg, 58%). ES-MS m/z 376.3 (MH+); HPLC RT (min) 3.94.

Workup

temperatureThe reaction mixture was cooled to rt
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2ac408fa649f4f2f8dfe08b9f4c83e7c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265144B2

Reaction notes

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