Cesium carbonate → HCID 68304682, compound

HRID 1616890Notes

Reaction equation

HRID 1616890 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16][CH:10]2[CH2:9]1)=O)(C)(C)C.Br[CH2:32][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[O:36]1[CH2:37][CH2:38][CH:33]([CH2:32][O:30][C:26]2[CH:25]=[C:24]([S:21]([C:18]3[CH:19]=[CH:20][C:14]4[CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]5[O:16][C:15]=4[CH:17]=3)(=[O:23])=[O:22])[CH:29]=[CH:28][CH:27]=2)[CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27732864-(Bromomethyl)oxaneHCID 53327613HCID 53327613, compound

Product 1

HCID 68304682HCID 68304682, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

7-(3-Hydroxy-benzenesulfonyl)-3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (enantiomer 2, 42 mg, 0.097 mmol) and 4-bromomethyl-tetrahydropyran (26 mg, 0.15 mmol) were dissolved in acetonitrile (1 ml). Cesium carbonate (95 mg, 0.29 mmol) was added, and the mixture was heated to 60° C. overnight. The solvent was evaporated and the residue purified by preparative TLC (30% EtOAc/hexane). The residue was dissolved in 1 mL of 4N HCl in dioxane (1 mL) and stirred for 2 h. The solvent was evaporated and the mixture was triturated with ether. The resulting solid was filtered, washed with ether (twice) and dried at 90° C. for 2 h. MS m/z 430 [M+H]+. 1H-NMR (400 MHz, CDCl3): δ 1.28-1.40 (m, 2H), 1.46-1.58 (m, 1H), 1.63-1.71 (m, 2H), 1.95-2.07 (m, 1H), 2.09-2.18 (m, 1H), 2.92-3.00 (m, 2H), 3.28-3.46 (m, 4H), 3.52-3.61 (m, 2H), 3.82-3.94 (m, 4H), 4.90-4.96 (m, 1H), 7.22-7.28 (m, 1H), 7.45 (s, 1H), 7.49-7.61 (m, 4H), 8.98 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative TLC (30% EtOAc/hexane)
  3. dissolutionThe residue was dissolved in 1 mL of 4N HCl in dioxane (1 mL)
  4. customThe solvent was evaporated
  5. customthe mixture was triturated with ether
  6. filtrationThe resulting solid was filtered
  7. washwashed with ether (twice) and
  8. customdried at 90° C. for 2 h

Sources & evidence

ORD record
ord-6514f708f1ca4c46af9b824009599df8
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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