Water → HCID 58368472, compound

HRID 515851Notes

Reaction equation

HRID 515851 reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[N:13]2)=[C:8]([Cl:23])[CH:7]=1)[CH3:5])=[N+]=[N-].O.CP(C)C>O1CCCC1.C(OCC)(=O)C>[Cl:23][C:8]1[CH:7]=[C:6]([CH:4]([NH2:1])[CH3:5])[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[N:13]2

Participants

6

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 58368577HCID 58368577, compound

Product 1

HCID 58368472HCID 58368472, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of peak 1 of 7-(1-azidoethyl)-5-chloro-8-(3-fluorophenyl)cinnoline (0.57 g, 1.7 mmol) from step N, in tetrahydrofuran (9.3 mL) and water (1.8 mL) was treated with 1 M of trimethylphosphine in tetrahydrofuran (2.1 mL, 2.1 mmol) and stirred at 20° C. for 30 minutes. The reaction mixture was diluted with ethyl acetate, washed with brine, dried with sodium sulfate, filtered, and concentrated to give the desired product (quantitative). This material was used without further purification. LCMS for C16H14ClFN3 (M+H)+: m/z=302.1; Found: 301.9.

Workup

  1. washwashed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6365c67c92ab4c13907f0b4b24e8b6d0
Source dataset
uspto-grants-2015_08
Patent number
US09108984B2

Reaction notes

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