Acetic Acid → 6-Iodo-2,3-dihydro-1H-indole

HRID 2046055Notes

Reaction equation

HRID 2046055 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CC(O)=O>>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 27823135-Iodo-1H-indole

Product 1

HCID 138639056-Iodo-2,3-dihydro-1H-indoleYield 99.5%

Procedure

To a solution of 5-iodoindole (0.2 g; 0.82 mmol) in AcOH (5 ml) NaBH3CN (0.2 g; 3.8 mmol) was added at −10° C. under N2. After stirring for 1 h at room temperature the solvent was removed in vacuo and the residue was diluted to 30 ml with Et2O and washed with 1N NaOH (5 ml), H2O (2×5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.2 g; 99%), which was used in next step without further purification. 1H-NMR (CDCl3) 7.35 (s, 1H); 7.25 (d, 1H, J=8.15 Hz); 6.43 (d, 1H, J=8.15 Hz); 5.21 (bs, 1H); 3.54 (t, 2H, J=8.36 Hz); 2.99 (t, 2H, J=8.36 Hz).

Workup

  1. customwas removed in vacuo
  2. additionthe residue was diluted to 30 ml with Et2O
  3. washwashed with 1N NaOH (5 ml), H2O (2×5 ml), brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-57169d0a7a1d4449bc9bdd087d347491
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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