tert-Butyl-4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate → tert-Butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174077Notes

Reaction equation

HRID 2174077 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH:20]([C:22]3[O:23][C:24]4[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:25]=4[N:26]=3)[OH:21])[C:13]([O:18][CH3:19])=[CH:14][C:15]=2[CH3:17])[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:31]([C:28]1[CH:29]=[CH:30][C:24]2[O:23][C:22]([C:20]([C:12]3[C:13]([O:18][CH3:19])=[CH:14][C:15]([CH3:17])=[C:16]4[C:11]=3[CH:10]=[CH:9][N:8]4[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[O:21])=[N:26][C:25]=2[CH:27]=1)#[N:32]

Participants

4

Reactant 1

HCID 86701709tert-Butyl-4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-((5-cyanobenzo[d]oxazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (163 mg, 0.376 mmol) was dissolved in DCM (3.76 mL) and MnO2 (327 mg, 3.76 mmol) was added. The reaction mixture was stirred at rt for 15 h. The reaction mixture was filtered through Celite® and washed three times with DCM. The filtrate was evaporated to dryness to give the title compound. MS (ESI+) m/z 432.16 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashed three times with DCM
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-4d65bee4f7104ef48a66722257c42bc0
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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