Potassium Iodide → HCID 86640829, compound

HRID 1675763Notes

Reaction equation

HRID 1675763 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]1[CH2:9][CH2:8][C:7]2([C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH2:10]2)[CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C=O)C>[C:33]([O:32][C:30](=[O:31])[CH2:29][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]2([CH2:8][CH2:9][N:4]([CH2:3][C:2]([F:1])([F:18])[F:19])[CH2:5][CH2:6]2)[CH2:10]1)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 67337882HCID 67337882, compound

Product 1

HCID 86640829HCID 86640829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1′-(2,2,2-trifluoroethyl)-1,2-dihydrospiro[indole-3,4′-piperidine] from Step A (64.0 mg, 0.237 mmol), potassium carbonate (49.0 mg, 0.355 mmol), potassium iodide (59.0 mg, 0.355 mmol), and tert-butyl bromoacetate (0.042 mL, 0.284 mmol) in DMF (2 mL) was stirred at 50° C. for 1 h. The reaction mixture was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (3×20 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=385 (M+1).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce1f3e65000d48b088f6351bc5c2badf
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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