Water → HCID 18332409, compound

HRID 2268769Notes

Reaction equation

HRID 2268769 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](OCC)(=[O:26])[CH3:25].O>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:25][CH2:24][OH:26])[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 18332409HCID 18332409, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (1.0 g, 0.00462 mol) and triethylamine (0.77 ml, 0.00555 mol) in DMF (60 ml), was added dropwise under nitrogen 2-bromoethanol (0.42 ml, 0.00555 mol) then allowed to stir at room temperature overnight. Workup involved addition of ethyl acetate (80 ml) and water (50 ml), the organic layer was washed with water (4×50 ml). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 2-(4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl)ethanol as a yellow solid 1.02 g.

Workup

  1. washthe organic layer was washed with water (4×50 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13ef95b2d42946a4a4b07a2a31721399
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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