Pyridine → N-[2-(2,3,7,8-Tetrahydrofuro[2,3-g]indol-1-yl)ethyl]acetamide

HRID 1781322Notes

Reaction equation

HRID 1781322 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[CH:2]1.[N:13]1[CH:18]=[CH:17]C=[CH:15][CH:14]=1.C(OC(=O)C)(=[O:21])C>C1COCC1>[N:1]1([CH2:15][CH2:14][NH:13][C:18](=[O:21])[CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH2:11][CH2:10][C:8]3=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22282663HCID 22282663, compound

Product 1

HCID 5311134N-[2-(2,3,7,8-Tetrahydrofuro[2,3-g]indol-1-yl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 7 (77 mg) in dry THF (5 ml) containing pyridine (0.09 ml) was added acetic anhydride (0.06 ml). After 18 h at 20° C. the mixture was partitioned between 2N Na2CO3 (30 ml) and EtOAc (2×30 ml). The dried extracts were evaporated and the residue chromatographed on silica gel (20 g). Elution with System A (200:8:1) gave the title compound as a colourless crystalline solid (56 mg), m.p. 126°-7° C.

Workup

  1. customAfter 18 h at 20° C. the mixture was partitioned between 2N Na2CO3 (30 ml) and EtOAc (2×30 ml)
  2. customThe dried extracts were evaporated
  3. customthe residue chromatographed on silica gel (20 g)
  4. washElution with System A (200:8:1)

Sources & evidence

ORD record
ord-369807e9e22041ffb2a801a6f750a115
Source dataset
uspto-grants-1997_05
Patent number
US05633276

Reaction notes

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