Sodium Iodide → HCID 123550853, compound

HRID 595194Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.CS(O[CH:20]([CH:22]1[CH2:26][C:25](=[O:27])[N:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[CH2:23]1)[CH3:21])(=O)=O.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:38][O:37][C:30]1[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=1[CH2:28][N:24]1[CH2:23][CH:22]([CH:20]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH3:21])[CH2:26][C:25]1=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 5.0 mmol), 1-[1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-3-yl]ethyl methanesulfonate (1.5 g, 4.2 mmol), NaI (64.0 mg, 0.04 mmol) and K2CO3 (1.2 g, 8.4 mmol) in DMF (15 mL) was stirred at 80° C. for 8 hours. The mixture was then diluted with water and extracted with EtOAc. The EtOAc layer was dried over sodium sulfate and concentrated under reduced pressure to afford racemic 1-(2,4-dimethoxybenzyl)-4-{1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-2-one which was used in next step without purification. MS ESI calc'd. for C24H35BN3O5 [M+H]+ 456. found 456.

Workup

extractionextracted with EtOAc
dry with materialThe EtOAc layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-04e45a1d8b154ed38cdfe817ce0a91a6
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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