7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester → 3-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

HRID 1616894Notes

Reaction equation

HRID 1616894 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30]CC5C=CC=CC=5)[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16][C:10]=2[CH2:9]1)=O)(C)(C)C>CO.CCOC(C)=O.[Pd]>[CH2:9]1[C:10]2[O:16][C:15]3[CH:17]=[C:18]([S:21]([C:24]4[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=4)(=[O:22])=[O:23])[CH:19]=[CH:20][C:14]=3[C:11]=2[CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 1

HCID 673238427-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester

Product 1

HCID 673256153-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol) in 5 mL methanol and 1 mL EtOAc was added Pd black (10% on carbon, 45 mg, 3.4 mmol). The mixture was kept under hydrogenation at 40 psi overnight and the solvent was evaporated. After filtration, the debenzylated product was taken to the next step without further purification. Removal of N-Boc protecting group with 4N HCl using a general procedure afforded the title product. mp 279-281° C., MS m/z 330 [M+H]+. 1H-NMR (400 MHz, DMSOd6): δ 10.26 (s, 1H), 9.76 (br s, 2H), 8.24 (s, 1H), 7.84 (m, 2H), 7.39 (m, 2H), 7.30 (s, 1H), 7.02 (m, 1H), 4.47 (s, 2H), 3.44 (m, 2H), 2.94 (m, 2H).

Workup

  1. customwas kept under hydrogenation at 40 psi overnight
  2. customthe solvent was evaporated
  3. filtrationAfter filtration
  4. customthe debenzylated product was taken to the next step without further purification
  5. customRemoval of N-Boc protecting group with 4N HCl using a general procedure

Sources & evidence

ORD record
ord-69dd6b55d4d649cf90285eb491d637a9
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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