Lithium Hydroxide → HCID 68109710, compound

HRID 2179367Notes

Reaction equation

HRID 2179367 reaction equation
C(OC([N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([O:38][CH3:39])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=O)C.[OH-].[Li+]>O1CCCC1.CO.O>[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([O:38][CH3:39])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][N:26]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 70565636HCID 70565636, compound

Product 1

HCID 68109710HCID 68109710, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product of step D (25 mg, 0.04 mmol), lithium hydroxide (14 mg, 0.32 mmol) in tetrahydrofuran (1.25 mL), methanol (0.62 mL) and water (0.31 mL) was stirred at ambient temperature for 8 h. The reaction was quenched with aqueous ammonium chloride (15 mL) and extracted with dichloromethane. The organic extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate) to give tert-butyl 8-((1H-indol-5-yl)sulfonyl)-6-methoxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (18 mg, 83%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.62 (s, 1H), 8.33 (s, 1H), 7.77-7.62 (m, 2H), 7.75 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 7.35-7.30 (m, 1H), 6.70-6.64 (m, 1H), 4.53 (s, 2H), 4.02 (s, 3H), 3.80 (t, J=5.4 Hz, 2H), 2.92-2.76 (m, 2H), 1.50 (s, 9H).

Workup

  1. customThe reaction was quenched with aqueous ammonium chloride (15 mL)
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1b3e00ba06fb4c96996404d1832de336
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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