Methanol → HCID 59813593, compound

HRID 1925327Notes

Reaction equation

HRID 1925327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:24]=[N:25][C:26]([O:29]C)=[CH:27][CH:28]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C[Si](I)(C)C.CO>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:28]=[CH:27][C:26](=[O:29])[NH:25][CH:24]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 59813813HCID 59813813, compound

Product 1

HCID 59813593HCID 59813593, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution/suspension of N-(3-chloro-4-fluorophenyl)-6-((6-(methoxy)-3-pyridinyl)oxy)-1-naphthalenecarboxamide (167 mg, 0.39 mmol) in chloroform (4.7 mL) was added trimethylsilyl iodide (Aldrich, 221 mg, 1.10 mmol). The reaction mixture was heated at 70° C. (oil bath) for 2.5 h, cooled to RT and MeOH (1 mL) was added. After stirring for 15 min, the dark yellow solution was concentrated in vacuo and treated with concentrated aqueous NH4OH (3 mL). The title compound was isolated by filtration and dried under high vacuum. MS (ESI, pos. ion) m/z: 409.1 (M+1). Mass Calc'd for C22H14ClFN2O3: 408.81.

Workup

  1. temperaturecooled to RT
  2. concentrationthe dark yellow solution was concentrated in vacuo
  3. additiontreated with concentrated aqueous NH4OH (3 mL)

Sources & evidence

ORD record
ord-ffa04a12d14f4b4eaf4fbcc2da420b2f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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