Acetic Anhydride → HCID 70974575, compound

HRID 1424546Notes

Reaction equation

HRID 1424546 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]#[C:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[C:5]([F:18])=[C:4]([F:19])[N:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]#[C:10][C:11]2[CH:17]=[CH:16][C:14]([NH:15][C:20](=[O:22])[CH3:21])=[CH:13][CH:12]=2)[C:5]([F:18])=[C:4]([F:19])[N:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68578502HCID 68578502, compound

Product 1

HCID 70974575HCID 70974575, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into the solution of 4-((Perfluoropyridin-4-yl)ethynyl)aniline, (13a) (0.158 g, 0.59 mmol) in 3 mL of CH2Cl2 were added acetic anhydride (0.134 g, 1.26 mmol) and Et3N (0.128 g, 1.26 mmol). The reaction mixture was stirred at room temperature overnight. After concentrating the solution in vacuo, the product was isolated by column chromatography (EtOAc:Hexane=1:2 to 1:1) with 85% yield: 1H-NMR (400 MHz, CD3OD) δ 7.70 (d, J=8.6 Hz, 2H), 7.59 (d, J=8.6 Hz, 2H), 2.15 (s, 3H); 13C-NMR (150 MHz, CD3CN) δ 170.1, 144.5 (dm, J=237 Hz), 143.1 (dm, J=259 Hz), 142.7, 134.2, 120.0, 115.4, 107.5 (t, J=3.4 Hz), 73.6 (t, J=4.3 Hz), 24.5; HRMS (ESI+): calcd for C15H9F4N2O1 [M+H]+ 309.06510, found 309.06678; m.p. 189-190° C.

Workup

  1. concentrationAfter concentrating the solution in vacuo
  2. customthe product was isolated by column chromatography (EtOAc:Hexane=1:2 to 1:1) with 85% yield

Sources & evidence

ORD record
ord-80ff7553783d4109b3fd85633d938fac
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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