1H-Indazole-5-carboxaldehyde → HCID 67085250, compound

HRID 1484566Notes

Reaction equation

HRID 1484566 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH2:12][C:13]([CH:17]([F:19])[F:18])=[CH:14][C:15]#[N:16]>C(O)(=O)C.C1COCC1>[F:18][CH:17]([F:19])[C:13]1[NH:12][C:13]([CH:17]([F:19])[F:18])=[C:14]([C:15]#[N:16])[CH:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 2

HCID 212506441H-Indazole-5-carboxaldehydeHCID 762236343-Amino-4,4-difluorobut-2-enenitrile

Product 1

HCID 67085250HCID 67085250, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 80 mg (0.55 mmol) 1H-indazole-5-carbaldehyde, 142 mg (1.21 mmol) 3-amino-4,4-difluorobut-2-enenitrile [obtainable by Thorpe reaction of acetonitrile with 2,2-difluoroacetonitrile, cf. Org. React. 15, 1 (1967), ibid. 1 (1984)] and a trace amount of powdered 4 Å molecular sieve in acetic acid (0.53 ml) was heated to reflux temperature for 5 h. After cooling, the reaction mixture was diluted with THF and filtered. The filtrate was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) yielding 95 mg (48% of th.) of the title compound.

Workup

  1. temperatureto reflux temperature for 5 h
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customThe filtrate was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-935cdf6d838b485aadf498f4e0915ba1
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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