(+/-)-tert-Butyl 4-((tert-butylsulfinylimino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate → tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174086Notes

Reaction equation

HRID 2174086 reaction equation
[C:1]([S:5]([N:7]=[C:8]([C:28]1[O:29][C:30]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:31]=2[N:32]=1)[C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH3:20])=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:39][Mg]Cl>C1COCC1.[NH4+].[Cl-].CCOC(C)=O>[C:37]([C:34]1[CH:35]=[CH:36][C:30]2[O:29][C:28]([C:8]([C:9]3[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH3:20])=[C:14]4[C:10]=3[CH:11]=[CH:12][N:13]4[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([NH:7][S:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[O:6])[CH3:39])=[N:32][C:31]=2[CH:33]=1)#[N:38]

Participants

6

Reactant 2

HCID 86701721(+/-)-tert-Butyl 4-((tert-butylsulfinylimino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 86701723tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of tert-butyl 4-((tert-butylsulfinyl)imino)(5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 130-A) (0.56 g, 1.047 mmol) in THF (10.47 mL), MeMgCl (3M in THF, 1.047 mL, 3.14 mmol) was added at 0° C. After 10 minutes the mixture was diluted with sat. aq. NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc, and the organic extract was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (0-100% EtOAc:Heptanes) to provide the title compound. MS (ESI+) m/z 551.2 (M+H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. extractionthe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (0-100% EtOAc:Heptanes)

Sources & evidence

ORD record
ord-2f9d76771c6c4df0be6741a3ab789903
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…