Hydrochloric Acid → HCID 89500787, compound

HRID 1844586Notes

Reaction equation

HRID 1844586 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](B(O)O)=[CH:11][C:10]2[S:16][C:17]([Cl:19])=[CH:18][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[C:23]([O:32][CH3:33])[C:24](=[CH:26]N(CC)CC)[N:25]=1.[O-:34]P([O-])([O-])=O.[K+].[K+].[K+].Cl>O.O1CCOCC1>[Cl:19][C:17]1[S:16][C:10]2[CH:11]=[C:12]([C:21]3[NH:25][C:24]([CH:26]=[O:34])=[C:23]([O:32][CH3:33])[CH:22]=3)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]=2[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 57353644N-[(5-bromo-3-methoxypyrrol-2-ylidene)methyl]-N-ethylethanamineHCID 89500809HCID 89500809, compound

Product 1

HCID 89500787HCID 89500787, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(tert-butoxycarbonyl)-2-chloro-4H-thieno[3,2-b]pyrrol-5-ylboronic acid (200 mg, 0.66 mmol), N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (160 mg, 0.61 mmol, provided by Chemzon Scientific Inc, Montreal, Canada), Pd(dppf)2Cl2CH2Cl2 (18 mg) and K3PO4 (260 mg) in a 20 mL sealed-tube flask was vented 4 times with nitrogen. 1,4-Dioxane (3 mL and water (0.4 mL) were introduced by syringes and the mixture was vented twice with nitrogen. The reaction mixture was heated at 80° C. for 1 h and TLC showed no starting materials were left. After being cooled to r.t., the reaction mixture was treated with 3 mL of 1N HCl, and stirred for 3 h. The mixture was then extracted with 20 mL of EtOAc, and the extract was dried over Na2SO4, filtered through a pad of silica gel. The filtrate was concentrated under vacuum and the residue was purified by Combiflash on a silica gel column eluted with a gradient of up to 60% EtOAc/hexanes to give 11 mg of the title compound as a solid.

Workup

  1. waitwere left
  2. temperatureAfter being cooled to r.t.
  3. extractionThe mixture was then extracted with 20 mL of EtOAc
  4. dry with materialthe extract was dried over Na2SO4
  5. filtrationfiltered through a pad of silica gel
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe residue was purified by Combiflash on a silica gel column
  8. washeluted with a gradient of up to 60% EtOAc/hexanes

Sources & evidence

ORD record
ord-ba96e95130a241ab800966c00d716551
Source dataset
uspto-grants-2015_02
Patent number
US08946445B2

Reaction notes

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