Potassium Carbonate → HCID 178497511, compound

HRID 416004Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:10]1=[O:22].[CH3:32][O:33][C:34]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)=[O:35].C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:32][O:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([CH2:8][C@@H:9]3[CH2:13][CH2:12][N:11]([C@H:14]4[CH2:15][CH2:16][C@H:17]([O:20][CH3:21])[CH2:18][CH2:19]4)[C:10]3=[O:22])=[C:6]([Cl:23])[CH:5]=2)=[CH:38][CH:37]=1)=[O:35]

Participants

Conditions

Temperature: 80 °C

Procedure

Mix trifluoro-methanesulfonic acid 3,5-dichloro-4-[(R)-trans-1-(4-methoxy-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-phenyl ester (2.134 g, 4.24 mmol), (4-methoxycarbonylphenyl)boronic acid (0.926 g, 5.09 mmol), tetrakis(triphenylphosphine)palladium(0) (0.490 g, 0.42 mmol) and 6.36 ml of 2M solution of K2CO3 in DME (10 mL). Stir for 12 hours at 80° C. Quench the reaction with water and extract with ethyl acetate. Wash the extract with brine and dry over magnesium sulfate. Purify by flash chromatography to recover 1.68 g (81%) of the title compound: MS (m/z): 490 (M+).

Workup

customQuench
customthe reaction with water
extractionextract with ethyl acetate
washWash the
extractionextract with brine
dry with materialdry over magnesium sulfate
customPurify by flash chromatography
customto recover 1.68 g (81%) of the title compound

Sources & evidence

ORD record: ord-8ffff9c734394134bd28e4f448039973
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088776B2

Reaction notes

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