Hydrochloric Acid → HCID 57484115, compound

HRID 1715590Notes

Reaction equation

HRID 1715590 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].C1(C)C=CC=CC=1.CCO>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1140TolueneHCID 574187505-Fluoro-2-[(1-methyl-1H-indazol-5-yl)oxy]benzonitrile

Product 1

HCID 57484115HCID 57484115, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Intermediate (4t) (1.13 g, 4.23 mmol; prepared as in Example 94, Steps A-C) was dissolved in methanol (50 mL) and 20% palladium hydroxide on activated carbon (0.50 g, 0.71 mmol) was added to the solution under nitrogen atmosphere. After the addition of concentrated HCl (12 N, 5.0 mL, 60 mmol), the mixture was stirred under hydrogen atmosphere overnight (18 hours). The mixture was filtered and palladium hydroxide was washed with MeOH. After evaporation, the crude residue was azeotroped with a mixture of toluene and EtOH to dryness to compound (5t) as a white powder (1.29 g, 99% yield) 1HNMR (400 MHz, CDCl3) δ 8.72 (br, 3H), 8.01 (s, 1H), 7.73 (d, J=8.6 Hz, 1H), 7.57 (dd, J=9.4, 2.3 Hz, 1H), 7.38 (s, 1H), 7.19 (d, J=3.1 Hz, 1H), 7.04 (td, J=74.8, 3.1 Hz, 1H), 7.02 (dd, J=195.1, 4.7 Hz, 1H), 4.07 (s, 3H) ppm.

Workup

  1. filtrationThe mixture was filtered
  2. washpalladium hydroxide was washed with MeOH
  3. customAfter evaporation

Sources & evidence

ORD record
ord-c8eaa0a7db5c4da1875a655cc7df3613
Source dataset
uspto-grants-2010_09
Patent number
US07799782B2

Reaction notes

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