4-Isocyanatopyridine → HCID 90102283, compound

HRID 1052509Notes

Reaction equation

HRID 1052509 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].[N:18]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)=[C:19]=[O:20]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:3]=1[NH:4][C:19]([NH:18][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)=[O:20]

Participants

5

Reactant 2

HCID 116367964-IsocyanatopyridineHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 90102283HCID 90102283, compoundYield 128.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (100 mg, 0.42 mmol) and 4-isocyanatopyridine (56 mg, 0.47 mmol) in tetrahydrofuran (2 ml) was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure to give 193 mg (100% yield) of the title compound. This crude was used in the following step without any further purification. Purity 77%.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f246f8707d0c47dc8e9f77a7e69ebc5d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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