Sodium Carbonate → HCID 67973310, compound

HRID 1184696Notes

Reaction equation

HRID 1184696 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].Br[C:32]1[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=1[CH3:40].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:32]4[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=4[CH3:40])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfaneHCID 67973765HCID 67973765, compound

Product 1

HCID 67973310HCID 67973310, 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 (150 mg), 1-bromo-2-methyl-4-methylsulfanyl-benzene (60 mg), in N,N-dimethylformamide (3 mL) a 2 M aqueous Na2CO3 solution (0.29 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added. The resulting mixture is stirred for 6 h at 90° C. After cooling to room temperature, water and methanol are added and the aqueous phase is extracted with ethyl acetate. The organic phase is concentrated and the residue is purified by HPLC on reversed phase (MeOH/H2O/TFA). Yield: 56 mg (56% of theory); LC (method 2): tR=1.70 min; Mass spectrum (ESI+): m/z=426 [M+H]+.

Workup

  1. customThe mixture is sparged with argon for 10 min
  2. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater and methanol are added
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. concentrationThe organic phase is concentrated
  7. customthe residue is purified by HPLC on reversed phase (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-2b250d6587684415a512c5dc60611b13
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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