Indole → HCID 68108773, compound

HRID 2179332Notes

Reaction equation

HRID 2179332 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl[S:13]([C:16]1[CH:17]=[CH:18][C:19]2[O:28][C:27]3[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][C:22]=3[C:20]=2[CH:21]=1)(=[O:15])=[O:14]>C1COCC1>[N:3]1([S:13]([C:16]2[CH:17]=[CH:18][C:19]3[O:28][C:27]4[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][C:22]=4[C:20]=3[CH:21]=2)(=[O:15])=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 86667995HCID 86667995, compound

Product 1

HCID 68108773HCID 68108773, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 19 mg, 0.484 mmol) was added to a solution of indole (42 mg, 0.363 mmol) in THF (1.5 mL) under N2 at room temperature, and the reaction stirred for 30 min. The product of step B (90 mg, 0.242 mmol) was then added and the reaction held for 2 h. It was quenched with H2O (10 mL), diluted with ether (10 mL) and the organic phase removed. The aqueous phase was extracted with ether (2×10 mL) and the combined organic phases dried over Na2SO2 and concentrated. Purification by combiflash (silica gel, hexane/ethyl acetate, 100:0 to 40:60) provided tert-butyl 8-(1H-indol-1-yl-sulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (28 mg, 25%) as a clear oil. 1H NMR (CDCl3, 300 MHz) δ 8.02 (d, J=9.0 Hz, 2H), 7.76 (dd, J=9.1, 2.2 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.33 (t, J=1.4 Hz, 1H), 7.28 (t, J=1.4 Hz, 1H), 6.66 (d, J=3.6 Hz, 1H), 4.53 (br s, 2H), 3.80 (t, J=6.2 Hz, 2H), 2.82 (t, J=6.2 Hz, 2H), 1.52 (s, 9H).

Workup

  1. waitthe reaction held for 2 h
  2. customIt was quenched with H2O (10 mL)
  3. additiondiluted with ether (10 mL)
  4. customthe organic phase removed
  5. extractionThe aqueous phase was extracted with ether (2×10 mL)
  6. dry with materialthe combined organic phases dried over Na2SO2
  7. concentrationconcentrated
  8. customPurification by combiflash (silica gel, hexane/ethyl acetate, 100:0 to 40:60)

Sources & evidence

ORD record
ord-d9f6e5df56204f99bc2f0dc662125bf4
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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