Water → 2-(2,5-dimethyl-1H-indol-3-yl)-benzoxazole

HRID 418430Notes

Reaction equation

HRID 418430 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:11])=[CH:6][CH:5]=2.Cl[C:13]1[O:14][CH:15]=[CH:16][N:17]=1.CN1[C:23](=O)[CH2:22][CH2:21][CH2:20]1.O>CCOC(C)=O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:13]1[O:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[N:17]=1)=[CH:8][C:7]([CH3:11])=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 709652,5-Dimethyl-1H-indoleHCID 133710742-Chloro-1,3-oxazole

Product 1

HCID 684575182-(2,5-dimethyl-1H-indol-3-yl)-benzoxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,5-dimethyl indole (0.3 g), 2-chlorooxazole (0.47 g) and NMP (2 ml) were heated in a microwave at 100 watts for 20 min at 160° C. Water ane EtOAc were added and separated, the aqueous phase was re-extracted with EtOAc (×4). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The precipitate was triturated with EtOAc then recrystallised from methanol to give the title compound (0.19 g).

Workup

  1. customseparated
  2. extractionthe aqueous phase was re-extracted with EtOAc (×4)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe precipitate was triturated with EtOAc
  6. customthen recrystallised from methanol

Sources & evidence

ORD record
ord-1c7720cdc9f248b9ade995052acb0d4c
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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