Hydrochloric Acid → HCID 57484115, compound

HRID 909164Notes

Reaction equation

HRID 909164 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[N:15]=[CH:14]3)=[C:6]([CH:9]=1)[C:7]#[N:8].[ClH:21]>CO.[OH-].[OH-].[Pd+2]>[ClH:21].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[N:15]=[CH:14]3)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574187505-Fluoro-2-[(1-methyl-1H-indazol-5-yl)oxy]benzonitrile

Product 1

HCID 57484115HCID 57484115, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (4t) (0.32 g, 1.22 mmol) in MeOH (20 mL) was purged with nitrogen and treated with 20% Pd(OH)2/C catalyst (15% wt, 180 mg) followed by concentrated HCl (0.3 mL, 3.6 mmol). After purging further with nitrogen, a balloon containing hydrogen was placed on top of the flask. After stirring at room temperature for 18 hours, the LC indicated no more starting material was present. The catalyst was filtered through a plug of silica gel/celite/sand and washed with MeOH. The solvent was evaporated in vacuo and the residue co-evaporated from ether. The resulting pale yellow foam (5t) was stored under N2, 0.34 g (91% isolated yield). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 272 (M+H) detected.

Workup

  1. customAfter purging further with nitrogen
  2. additiona balloon containing hydrogen
  3. filtrationThe catalyst was filtered through a plug of silica gel/celite/sand
  4. washwashed with MeOH
  5. customThe solvent was evaporated in vacuo
  6. custom0.34 g (91% isolated yield)

Sources & evidence

ORD record
ord-06d16a2c60a74ee0a46ab208a32b5898
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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