2-Chloro-6-fluoroaniline → HCID 90040573, compound

HRID 1485894Notes

Reaction equation

HRID 1485894 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]1[C:18]([OH:20])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:23]=1[NH2:24]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]1[C:18](=[O:20])[NH:24][C:23]1[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:22]=1[Cl:21])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 27342052-Chloro-6-fluoroanilineHCID 25417906HCID 25417906, compound

Product 1

HCID 90040573HCID 90040573, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of (S)-3,4-dihydro-1H-isoquinoline-1,2-dicarboxylic acid 2-tert-butyl ester (100 mg, 361 μmol, Eq: 1) and 2-chloro-6-fluoroaniline (63.0 mg, 433 μmol, Eq: 1.2) in pyridine (2.00 mL) at 0° C. was added POCL3 (82.9 mg, 50.4 μL, 541 μmol, Eq: 1.5). Reaction was warmed to RT and stirred for 2 h. The mixture was evaporated and water was added to the residue. The mixture was extracted with EtOAc, the combined organics were washed with water, brine, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography to give (S)-1-(2-chloro-6-fluoro-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (79 mg) as a white solid.

Workup

  1. customReaction
  2. customThe mixture was evaporated
  3. additionwater was added to the residue
  4. extractionThe mixture was extracted with EtOAc
  5. washthe combined organics were washed with water, brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-105b643aeae244b684468ca3bd91f5f8
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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