Tetrahydrofuran → HCID 69307203, compound

HRID 1947029Notes

Reaction equation

HRID 1947029 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=1.C1C[O:30]CC1>>[CH3:26][S:25]([C:21]1[N:20]=[C:19]([N:14]2[C:15]3[C:11](=[C:10]([CH2:9][O:5][CH2:4][CH2:3][S:2][CH3:1])[CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)[CH:24]=[CH:23][N:22]=1)=[O:30]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 789252-(Methylthio)ethanolHCID 69312027HCID 69312027, compound

Product 1

HCID 69307203HCID 69307203, compound

Procedure

2-methylsulfanyl-ethanol (0.29 mL, 3.36 mmol) was dissolved in THF (5 mL), cooled in an ice bath, and NaH (148 mg, 3.7 mmol) was the added portionwise. After 30 min, a suspension of 4-bromomethyl-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indole (750 mg, 2.24 mmol) in THF (5 mL) was added, and the mixture was stirred at RT overnight. The mixture was then concentrated in vacuo, and the residue purified using flash chromatography on a silica column, eluting with hexane:ethyl acetate 4:1 to 3:7 to yield 1-(2-methanesulfinyl-pyrimidin-4-yl)-4-(2-methylsulfanyl-ethoxymethyl)-1H-indole (390 mg).

Workup

  1. temperaturecooled in an ice bath
  2. additionadded portionwise
  3. additionwas added
  4. concentrationThe mixture was then concentrated in vacuo
  5. customthe residue purified
  6. washeluting with hexane:ethyl acetate 4:1 to 3:7

Sources & evidence

ORD record
ord-da0985e46dac4d0a99420e891cda7633
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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