Iodoethane → HCID 10204220, compound

HRID 889887Notes

Reaction equation

HRID 889887 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C:13]1[S:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27]([CH3:32])=[CH:26]3)[CH:14]=1)=[O:12].[CH2:33](I)[CH3:34]>CN(C=O)C>[CH2:33]([N:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][C:19]3[CH:18]=[CH:17][N:16]=[C:15]4[CH:14]=[C:13]([C:11]([N:7]5[CH2:8][CH2:9][CH2:10][C@@H:6]5[CH2:5][O:4][CH3:3])=[O:12])[S:21][C:20]=34)=[CH:31][CH:30]=2)[CH:26]=[C:27]1[CH3:32])[CH3:34]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10159192HCID 10159192, compound

Product 1

HCID 10204220HCID 10204220, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (16 mg, 0.4 mmol) was added to a solution of (2R)-(2-methoxymethyl-pyrrolidin-1-yl)-[7-(2-methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone (85 mg, 0.2 mmol) in DMF (5 mL), at 0° C. The reaction mixture was allowed to stir for 20 min, and EtI (57 mg, 0.40 mmol) was added dropwise. After 3 h the reaction was quenched with saturated aqueous KCN (10 mL). The aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4), and the solvent was removed. Purification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6) afforded the title compound as a white solid (46 mg, 51%). MS: 450 (MH+); HPLC Rf: 6.83 min; HPLC purity: 95%.

Workup

  1. customAfter 3 h the reaction was quenched with saturated aqueous KCN (10 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customthe solvent was removed
  5. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6)

Sources & evidence

ORD record
ord-d5b1d952250f4833879660d9d329517b
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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