Sodium Carbonate → HCID 59843041, compound

HRID 1878708Notes

Reaction equation

HRID 1878708 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:18])[N:6]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:18]=[C:5]1[CH:4]=[CH:3][C:2]([C:20]2[S:19][CH:23]=[CH:22][CH:21]=2)=[CH:7][N:6]1[CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 59843078HCID 59843078, compound

Product 1

HCID 59843041HCID 59843041, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of tert-butyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)ethylcarbamate (166 mg, 523 μmol), 2-thiopheneboronic acid (134 mg, 1047 μmol), Na2CO3 (785 μl, 1570 μmol) [2M], and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (31 mg, 42 μmol) in DME (2 mL) was heated to 85° C. for 45 min. The mixture was partitioned between CH2Cl2 and 10% Na2CO3 and the aqueous was extracted with CH2Cl2 (10 mL). The combined organics were dried over MgSO4 and purified on silica (12 g) eluting with 0>50% of 5% MeOH/CH2Cl2, and isolated as orange crystals from ACN. MS (ESI pos. ion) m/z (MH+): 321 (MH+). Calc'd exact mass for C16H20N2O3S: 320. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.42 (s, 9H) 3.51 (q, J=6.00 Hz, 2H) 4.14 (t, J=5.67 Hz, 2H) 4.96 (br. s., 1H) 6.63 (d, J=9.39 Hz, 1H) 7.01-7.09 (m, 2H) 7.23 (dd, J=4.99, 1.27 Hz, 1H) 7.47-7.51 (m, 1H) 7.61 (dd, J=9.39, 2.54 Hz, 1H).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 10% Na2CO3
  2. extractionthe aqueous was extracted with CH2Cl2 (10 mL)
  3. dry with materialThe combined organics were dried over MgSO4
  4. custompurified on silica (12 g)
  5. washeluting with 0>50% of 5% MeOH/CH2Cl2
  6. customisolated as orange crystals from ACN

Sources & evidence

ORD record
ord-4b47a34fa18c4551ba1822a700a2a8cd
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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