Sodium Iodide → HCID 123209511, compound

HRID 595196Notes

Reaction equation

CS(O[CH2:6][CH:7]1[CH2:11][C:10](=[O:12])[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[CH2:8]1)(=O)=O.[CH3:24][C:25]1([CH3:37])[C:29]([CH3:31])([CH3:30])[O:28][B:27]([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)[O:26]1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[CH2:8][CH:7]([CH2:6][N:35]2[CH:36]=[C:32]([B:27]3[O:26][C:25]([CH3:37])([CH3:24])[C:29]([CH3:31])([CH3:30])[O:28]3)[CH:33]=[N:34]2)[CH2:11][C:10]1=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of [1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-3-yl]methyl methanesulfonate (1.5 g, 4.2 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 5.0 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 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-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}pyrrolidin-2-one which was used in next step without purification. MS ESI calc'd. for C23H33BN3O5 [M+H]+ 442. found 442.

Workup

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

Sources & evidence

ORD record: ord-9ac8292a8a5d4a09bbde63ffbe1d262f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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