Sodium Carbonate → HCID 86594579, compound

HRID 1744143Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5](=[O:27])[CH:6]([S:11][C:12]1[CH:17]=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].Br[C:29]1[CH:43]=[CH:42][C:32]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([CH:6]([S:11][C:12]1[CH:13]=[CH:14][C:15]([C:29]2[CH:30]=[CH:31][C:32]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:42][CH:43]=2)=[CH:16][CH:17]=1)[CH2:7][CH:8]([CH3:9])[CH3:10])=[O:27])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(cyanomethyl)-4-methyl-2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]thio}pentanamide (1.64 g, 4.22 mmol) and tert-butyl 4-bromobenzylcarbamate (1.33 g, 4.64 mmol) were mixed in DMF (12 mL). After addition of sodium carbonate (7.4 mL of a 2.0 M solution, 14.8 mmol), the reaction flask was thoroughly degassed with dry nitrogen. PdCl2dppf (103 mg, 0.13 mmol) was added and the reaction mixture was heated at 80° C. for 4 h. Aqueous sat. NaHCO3 was added, the product was extracted with EtOAc (3×), dried over MgSO4, concentrated in vacuo, and purified by flash chromatography (40% EtOAc/hexanes) to afford tert-butyl {4′-[(1-{[(cyanomethyl)amino]carbonyl }-3-methylbutyl)thio]-1,1′-biphenyl-4-yl}methylcarbamate.

Workup

customwas thoroughly degassed with dry nitrogen
extractionthe product was extracted with EtOAc (3×)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by flash chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-73f82cf4b19b4cfaba9bf2dbc116bcc3
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012075B2

Reaction notes

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