Water → HCID 53358569, compound

HRID 1807311Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:38])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:36]=[CH:35]C(I)=CN=2)=O)[CH:5]=[CH:6][CH:7]=1.C[N:40]([CH:42]=O)[CH3:41].[C:44](=O)([O-:46])[O-:45].[K+].[K+].[OH2:50]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@:12]2([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[NH:10][C@@H:9]([C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:41]([C:44]([OH:46])=[O:45])=[N:40][CH:42]=3)=[O:50])[C@@H:8]2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:38])=[C:16]([F:22])[CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In a 50 ml pressure tube, (2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-N-(5-iodopyridin-2-yl)-5-neopentylpyrrolidine-2-carboxamide (100 mg, 149 μmol, Eq: 1.00) was combined with DMF (4 ml) and water (200 μl). Potassium carbonate (41.3 mg, 299 μmol, Eq: 2) was added. The mixture was bubbled with nitrogen and then palladium(II) acetate (4 mg, 17.8 μmol, Eq: 0.119) was added. The tube was subjected to CO atmosphere at 40 PSI and stirred overnight at 70° C.

Workup

customThe mixture was bubbled with nitrogen

Sources & evidence

ORD record: ord-9b6759e3381f40638828baed60e82ef9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354444B2

Reaction notes

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