Sodium Carbonate → HCID 67990247, compound

HRID 1184794Notes

Reaction equation

HRID 1184794 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].I[C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[N:36][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:32]4[CH:37]=[N:36][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1488682N-(5-iodopyridin-2-yl)acetamideHCID 67973765HCID 67973765, compound

Product 1

HCID 67990247HCID 67990247, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (41.5 mg) and N-(5-iodo-pyridin-2-yl)-acetamide (39.3 mg) in N,N-dimethylformamide (2 mL) a 2 M aqueous Na2CO3 solution (0.125 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (8 mg) is added. The resulting mixture is stirred over night at 90° C. After cooling to room temperature, the mixture is filtered over basic alumina and eluted with N,N-dimethyl-formamide/MeOH (9:1; 2 mL). The solvent is evaporated and the residue is purified by preparative HPLC (eluent water (+0.1% NH3)/MeOH) to yield the desired product. HPLC (method 13): tR=0.25 min; Mass spectrum (ESI+): m/z=424 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon for 10 min
  3. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (8 mg) is added
  4. temperatureAfter cooling to room temperature
  5. filtrationthe mixture is filtered over basic alumina
  6. washeluted with N,N-dimethyl-formamide/MeOH (9:1; 2 mL)
  7. customThe solvent is evaporated
  8. customthe residue is purified by preparative HPLC (eluent water (+0.1% NH3)/MeOH)

Sources & evidence

ORD record
ord-31e4c8496de14196aa1cc9bce0510a53
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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