Trifluoroacetic acid → HCID 25094494, compound

HRID 1095737Notes

Reaction equation

HRID 1095737 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.Br[CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C.[I-].C([NH3+])(C)(C)C.O.[OH-].[Cs+].C(O)(C(F)(F)F)=O>CN(C=O)C.CCOC(C)=O.O.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([O:25][CH2:27][CH2:28][NH2:29])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 22344722t-Butylammonium IodideHCID 23679066Caesium hydroxide--water (1/1/1)HCID 66781369HCID 66781369, compound

Product 1

HCID 25094494HCID 25094494, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

To 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (50 mg, 0.15 mmol) in DMF (3 mL) was added 4 angstrom molecular sieves (2 g), tert-butyl 2-bromoethylcarbamate (40 mg, 0.18 mmol), t-butylammonium iodide (3 mg) and cesium hydroxide hydrate (50 mg, 0.30 mmol). The reaction mixture was stirred overnight, then dilute with EtOAc/H2O (10 mL/10 mL). The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give crude, N-Boc-protected product, to which was added DCM (1 mL) and TFA (1 mL). This mixture was stirred for 30 minutes and then concentrated. The residue was purified by silica gel chromatography, eluting with DCM/MeOH/NH4OH (10:1:0.1) to provide the desired product (20 mg). APCI (+) m/z 379.2 (M+1) detected.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude, N-Boc-protected product
  6. stirringThis mixture was stirred for 30 minutes
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with DCM/MeOH/NH4OH (10:1:0.1)

Sources & evidence

ORD record
ord-2bf91442d400461aa8329496ea5eaeec
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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