Sodium Carbonate → HCID 24985251, compound

HRID 1724062Notes

Reaction equation

HRID 1724062 reaction equation
I[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH2:11][C:10]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[O:9][C:8]2=[O:17])=[CH:4][CH:3]=1.[CH2:20]([N:27]1[CH2:32][CH2:31][O:30][CH:29](B(O)O)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:27]1([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[C:2]2[CH:19]=[CH:18][C:5]([CH2:6][N:7]3[CH2:11][C:10]4([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[O:9][C:8]3=[O:17])=[CH:4][CH:3]=2)[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 57559818HCID 57559818, compoundHCID 68546700HCID 68546700, compound

Product 1

HCID 24985251HCID 24985251, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(4-Iodo-benzyl)-1-oxa-3-aza-spiro[4.5]decan-2-one (55 mg, 0.148 mmol) and benzylmopholine-2-boronic acid (49 mg, 0.222 mmol) were mixed in ethylene glycol dimethyl ether (1 mL) and sodium carbonate (2M) aqueous solution (1 mL). Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (17 mg, 0.0148 mmol) was added and the reaction mixture was heated at 100˜110° C. for 1˜1.5 hours. The reaction was diluted with dichloromethane (DCM), washed with water (4 mL) and brine (4 mL). The organic phase was separated, dried over anhydrous sodium sulfate and concentrated. The crude residue was purified on silica gel eluting with 5-30% ethyl acetate in hexane to give the product as off-white solid (52 mg, 83%). 1H NMR (300 MHz, CDCl3): δ 7.49 (m, 1H), 7.42 (d, 2H), 7.32 (m, 5H), 4.5 (s, 2H), 3.65 (t, 4H), 3.39 (s, 2H), 3.18 (s, 2H), 2.36 (t, 4H), 1.82 (m, 4H), 1.54 (m, 6H).

Workup

  1. temperaturethe reaction mixture was heated at 100˜110° C. for 1˜1.5 hours
  2. washwashed with water (4 mL) and brine (4 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude residue was purified on silica gel eluting with 5-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-175fe6edd2cc4854944d4916159c38a3
Source dataset
uspto-grants-2009_02
Patent number
US07485722B2

Reaction notes

Loading…