Iodoethane → HCID 86640258, compound

HRID 422106Notes

Reaction equation

HRID 422106 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[OH:23])=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[C:5]([F:24])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31](I)[CH3:32]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[O:23][CH2:31][CH3:32])=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[C:5]([F:24])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 86640256HCID 86640256, compound

Product 1

HCID 86640258HCID 86640258, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 4-[2-(2-chloro-5-fluoro-pyrimidin-4-yl)-benzo[b]thiophen-7-yl]-pyridin-3-ol (100 mg, 0.28 mmol) and cesium carbonate (100 mg, 0.28 mmol) in dimethylformamide (1 mL) with ethyl iodide (44 mg, 0.28 mmol). Stir the mixture at room temperature for 12 hours. Dilute the mixture with ethyl acetate and wash the solution with three portions of water, one portion of saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo. Purify the crude product by column chromatography on 12 g silica gel eluting with a gradient of dichloromethane to ethyl acetate to give the title compound (48 mg, 45%) as a brown solid. MS (ES) m/z 386 [M+1]+.

Workup

  1. washwash the solution with three portions of water, one portion of saturated aqueous sodium chloride
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the crude product by column chromatography on 12 g silica gel eluting with a gradient of dichloromethane to ethyl acetate

Sources & evidence

ORD record
ord-f8c5ba2e5d6b445a96bc4fb578530c5b
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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