Hydrochloric Acid → HCID 58382084, compound

HRID 1628075Notes

Reaction equation

HRID 1628075 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=3)[C:14]([O:16]C(C)(C)C)=[O:15])[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:5]2=[N:6][CH:7]=1.BrC1C=C(C=CC=1)C(OC(C)(C)C)=O.C[Si](C#C)(C)C.C([O-])([O-])=O.[K+].[K+].BrC1C(N)=NC=C(Br)N=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=3)[C:14]([OH:16])=[O:15])[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:5]2=[N:6][CH:7]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 334079tert-Butyl 3-bromobenzoateHCID 6200042-Amino-3,5-dibromopyrazineHCID 58382442HCID 58382442, compound

Product 1

HCID 58382084HCID 58382084, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 3-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoate (2.5 g, 4.96 mmol, prepared using A from tert-butyl 3-bromobenzoate [Frontier Scientific] with trimethylsilylacetylene, Q with K2CO3, A with 3,5-dibromopyrazin-2-amine, B and C) and K2CO3 (0.685 g, 4.96 mmol) in MeOH (20 mL) were added to a flask. The mixture was heated to about 60° C. for about 17 h. An aqueous 40% NaOH solution (2 mL) was added and the mixture was heated to about 60° C. for about 17 h. The mixture was cooled to rt and acidified with about 3 mL of 5 N aqueous HCl and then extracted with EtOAc (100 mL). The solids were removed by filtration then the filtrate was dried over anhydrous MgSO4 and concentrated under reduced pressure to provide 3-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoic acid (2.01 g, 90%): LC/MS (Table 2, Method b) Rt=2.80 min; MS m/z 448 (M+H)+.

Workup

  1. temperaturethe mixture was heated to about 60° C. for about 17 h
  2. temperatureThe mixture was cooled to rt
  3. extractionextracted with EtOAc (100 mL)
  4. customThe solids were removed by filtration
  5. dry with materialthe filtrate was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c86ef46c105f4ffaab259df1e3216e3f
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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