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

HRID 2174084Notes

Reaction equation

HRID 2174084 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:13]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O)=[N:8][C:7]=2[CH:32]=1)#[N:2].[CH3:33][C:34]([S:37]([NH2:39])=[O:38])([CH3:36])[CH3:35]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[C:34]([S:37]([N:39]=[C:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:32][C:7]=2[N:8]=1)[C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]2[C:14]=1[CH:15]=[CH:16][N:17]2[C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[O:38])([CH3:36])([CH3:35])[CH3:33]

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 86701711tert-Butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tert-butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 126-A) (711 mg, 1.648 mmol) and 2-methyl-2-propanesulfinamide (599 mg, 4.94 mmol) in toluene (16.5 mL), Zr(O-t-Bu)4 (4.33 mL, 8.24 mmol) was added at room temperature. After 2 hours the reaction mixture was diluted with EtOAc and brine. The resulting mixture was filtered through Celite® and the organic layer of the filtrate was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc:Heptanes) to provide the title compound. MS (ESI+) m/z 535.2 (M+H).

Workup

  1. filtrationThe resulting mixture was filtered through Celite®
  2. dry with materialthe organic layer of the filtrate was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (0-80% EtOAc:Heptanes)

Sources & evidence

ORD record
ord-769c205b4ea94055877c756120bd10c7
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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