2-Bromoethanol → HCID 18522132, compound

HRID 413797Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:22]2[C:17](=[C:18]([OH:23])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:24]([O:26][CH3:27])=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:29][CH2:30][OH:31]>CN(C=O)C>[CH2:7]([N:14]1[C:22]2[C:17](=[C:18]([O:23][CH2:29][CH2:30][OH:31])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:24]([O:26][CH3:27])=[O:25])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (0.2 g) was added to a stirred solution of methyl N-benzyl-4-hydroxyindole-2-carboxylate (0.2 g) and 2-Bromoethanol (98 mg) in DMF (15 ml). The reaction was then stirred for 16 hours at 80° C. under an atmosphere of argon. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with water, dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using 70% ethyl acetate: isohexane as eluent to give the product as a colourless crystalline solid. (64 mg, 27%); NMR d (CD3SOCD3) 3.74-3.82 (m, 5H), 4.10 (m, 2H), 4.88 (m, 1H), 5.80 (s, 2H), 6.58 (m, 1H), 6.98 (d, 2H), 7.09 (m, 1H), 7.14-7.27 (m, 4H), 7.38 (m, 1H); M/z (+) 326 (MH+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue partitioned between ethyl acetate and water
washCombined organic extracts were washed with water
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customthe residue purified by column chromatography

Sources & evidence

ORD record: ord-9436d38747fe48ed8c8b8a554adef36e
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569888B1

Reaction notes

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