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

HRID 2174104Notes

Reaction equation

HRID 2174104 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[NH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[OH:33])[C:28]#[N:29].C1N2CCN(CC2)C1>CN1C(=O)CCC1>[C:28]([C:27]1[CH:30]=[CH:31][C:32]2[O:33][C:2]([CH2:3][C:4]3[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]4[C:5]=3[CH:6]=[CH:7][N:8]4[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:24][C:25]=2[CH:26]=1)#[N:29]

Participants

5

Reactant 3

HCID 9237DabcoHCID 2712583-Amino-4-hydroxybenzonitrileHCID 86701482tert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of tert-butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 20-A) (0.720 g, 1.617 mmol) and 3-amino-4-hydroxybenzonitrile (0.325 g, 2.426 mmol) and DABCO (0.544 g, 4.85 mmol) in NMP (1.62 ml) was stirred at 100° C. for 16 hrs. The reaction mixture was cooled and loaded onto silica gel to purify via FCC eluting with Heptane/AcOEt:100/0 to 0/100 to obtain the title compound. MS (ESI+) m/z 418.34 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto purify via FCC
  3. washeluting with Heptane/AcOEt

Sources & evidence

ORD record
ord-dd5aef5fa38948db94189ec498604d37
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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