Cesium carbonate → HCID 66578796, compound

HRID 1529099Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH2:27])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.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.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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]>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.200 g, 0.552 mmol) and 3-bromo-pyridine (0.087 g, 0.552 mmol) were dissolved in toluene along with Pd(dba)2 (0.032 g, 0.055 mmol), BINAP (0.069 g, 0.11 mmol) and cesium carbonate (0.270 g, 0.828 mmol). The reaction was heated to 110° C. overnight then allowed to cool. The reaction mixture was filtered through Celite then purified via preparatory HPLC to afford the title

Workup

temperatureto cool
filtrationThe reaction mixture was filtered through Celite
customthen purified via preparatory HPLC
customto afford the title

Sources & evidence

ORD record: ord-cb8ce912133543abb1a3b071c8fd7930
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090573B2

Reaction notes

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