4-Tert-Butylaniline → HCID 21959540, compound

HRID 238524Notes

Reaction equation

HRID 238524 reaction equation
[F:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[C:16]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])=[CH:25][CH:26]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 516892Sodium BicarbonateHCID 219595822-Fluoropyridine-3-carbonyl chloride

Product 1

HCID 21959540HCID 21959540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-fluoropyridine-3-carbonyl chloride (3.2 g, 20 mmol, Step D) and NaHCO3 (4 g, 48 mmol) in CH2Cl2 added in dropwise a solution of 4-tert butylaniline (3.0 g, 20 mmol). After the addition, the suspension was stirred at RT for 5 h. Solid inorganic salts were removed via filtration. The filtrate was concentrated to afford a brown solid as desired compound. MS: 273 (M+H). Calc'd. for C16H17FN2O—272.33.

Workup

  1. additionAfter the addition
  2. customSolid inorganic salts were removed via filtration
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-841959ce031449ee8d8e6c98ad1ee3c1
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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