Ethyl Acetate → HCID 59403464, compound

HRID 1514182Notes

Reaction equation

HRID 1514182 reaction equation
Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]4[CH2:28][NH:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:29]=3)[N:15]=2)=[CH:10][C:7]=1[C:8]#[N:9])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].CCOC(C)=O>CN(C=O)C>[C:8]([C:7]1[CH:10]=[C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]4[CH2:28][N:27]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:26][CH2:25][CH2:24][C:23]=4[CH:29]=3)[N:15]=2)[CH:12]=[CH:13][C:6]=1[O:5][CH:3]([CH3:2])[CH3:4])#[N:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 68469902HCID 68469902, compound

Product 1

HCID 59403464HCID 59403464, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(1-Methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 3) (70 mg, 0.170 mmol) and caesium carbonate (167 mg, 0.511 mmol) in dry DMF (5 ml) were treated with tert-butyl bromoacetate (0.038 ml, 0.256 mmol) and stirred at RT for 3 hours to give a single product. EtOAc (40 ml) was added and the mixture washed with water (2×50 ml), dried over anhydrous MgSO4 and evaporated to yield the title compound (85 mg) as a clear, colourless oil. MS (ES) C28H32N4O4 requires 488; found 489 (M+H)+.

Workup

  1. customto give a single product
  2. washthe mixture washed with water (2×50 ml)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-47e59352bb514e12b4e2a3ecffc66977
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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