3-Chloro-4-fluoroaniline → HCID 59813813, compound

HRID 2115825Notes

Reaction equation

HRID 2115825 reaction equation
Cl.[CH3:2][O:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21](Cl)=[O:22])=[CH:16][CH:15]=[CH:14]3)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[Cl:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][C:40]=1[F:41])[NH2:37]>C(Cl)Cl>[Cl:33][C:34]1[CH:35]=[C:36]([NH:37][C:21]([C:17]2[C:18]3[C:13](=[CH:12][C:11]([O:10][C:7]4[CH:8]=[N:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=4)=[CH:20][CH:19]=3)[CH:14]=[CH:15][CH:16]=2)=[O:22])[CH:38]=[CH:39][C:40]=1[F:41]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 86608620HCID 86608620, compound

Product 1

HCID 59813813HCID 59813813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(6-methoxypyridin-3-yloxy)-1-naphthoyl chloride hydrochloride salt (225 mg, 0.64 mmol) and DIPEA (0.22 mL, 1.285 mmol) in DCM (5 mL) at RT was added 3-chloro-4-fluoroaniline (93.5 mg, 0.64 mmol). After stirring for 16 h, the reaction mixture was directly purified by silica gel chromatography (elution hexanes/EtOAC: 85/15 to 35/65) to give the title compound as a tan solid. MS (ESI, pos. ion) m/z: 423.1 (M+1). Mass Calc'd for C23H16ClFN2O3: 422.84.

Workup

  1. customthe reaction mixture was directly purified by silica gel chromatography (elution hexanes/EtOAC: 85/15 to 35/65)

Sources & evidence

ORD record
ord-2dbbee48488f47df890cd4ad86e73ac2
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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