Cesium carbonate → HCID 67222883, compound

HRID 876571Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[C@H:11]([OH:26])[C@H:12]2[O:17][CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=3)[C:13]2=[O:25])=[CH:5][CH:4]=1)#[N:2].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.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>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[C@H:11]([OH:26])[C@H:12]2[O:17][CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([C:29]4[S:28][CH:32]=[CH:31][CH:30]=4)=[CH:20][CH:19]=3)[C:13]2=[O:25])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of compound 14-4 (80 mg) in THF—H2O (2 mL-0.67 mL), were added 2-thiopheneboronic acid (43 mgl), Cs2CO3 (0.44 g), and Pd(Ph3P)4 (19.4 mg). The mixture was stirred at 80° C. for 15 hours. The reaction mixture was filtered with Celite® pad and rinsed with the mixed solvent (EtOAc-MeOH=1-1). The filtrate was concentrated in vacuo and the resulting residue was washed with H2O and Et2O. The precipitate was collected by filtration to obtain compound 22-1 (35 mg) as a pale brown amorphous solid.

Workup

filtrationThe reaction mixture was filtered with Celite® pad
washrinsed with the mixed solvent (EtOAc-MeOH=1-1)
concentrationThe filtrate was concentrated in vacuo
washthe resulting residue was washed with H2O and Et2O
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-bd1c0b8e8eda4b30850477d08f673f74
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987242B2

Reaction notes

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