Methyl bromoacetate → HCID 68182935, compound

HRID 1615585Notes

Reaction equation

HRID 1615585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[C:10]3[S:15][C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:17][C:9]2=3)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:11](=[O:14])[C:10]3[S:15][C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:17][C:9]2=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 68183085HCID 68183085, compound

Product 1

HCID 68182935HCID 68182935, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-(4-chlorophenyl)-2-morpholino-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (451 mg, 1.29 mmol) in THF (7.0 mL) in an ice bath was added 1.00 M potassium t-butoxide in THF (1.42 mL, 1.42 mmol) and the resulting solution was stirred in the ice bath for 30 minutes. Methyl bromoacetate (184 uL, 1.94 mmol) was added and the solution was stirred for 1 hour in the ice bath. The reaction was quenched with saturated NH4Cl (10 mL) and diluted with ethyl acetate (20 mL). The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→40/60) to give 455 mg (84% yield) of the title compound as a light yellow oil. LC/MS (FA) ES+ 421. 1H NMR (400 MHz, CDCl3) δ: 7.15-7.12 (m, 2H), 7.03-7.00 (m, 2H), 5.38 (s, 1H), 4.09 (d, 1H, J=17.2 Hz), 4.06-4.01 (m, 1H), 3.99 (d, 1H, J=17.2 Hz), 3.63-3.61 (m, 4H), 3.57-3.53 (m, 2H), 3.52 (s, 3H), 2.99-2.97 (m, 4H).

Workup

  1. customThe reaction was quenched with saturated NH4Cl (10 mL)
  2. additiondiluted with ethyl acetate (20 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→40/60)

Sources & evidence

ORD record
ord-81ee99e9260c4ad994ecf14fcb3de889
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

Loading…