6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde → 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-ol

HRID 588158Notes

Reaction equation

HRID 588158 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.[C:34]([Mg]Cl)#[CH:35]>>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[C:34]#[CH:35])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 1182719996-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehydeHCID 178462451HCID 178462451, compound

Product 1

HCID 1182719011-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-olYield 97.1%

Conditions

Temperature
-78 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (11B, 250 mg, 0.551 mmol) was added to a oven dried 20 mL microwave vial, charged with THF (10 ml), degassed under nitrogen and cooled to −78° C. To the mixture was added ethynylmagnesium chloride (1.322 ml, 0.661 mmol) dropwise and the reaction was slowly warmed to rt over 30 minutes. The reaction was quenched with saturated ammonium chloride, extracted 3×20 mL EtOAc, washed with brine, dried over sodium sulfate filtered and concentrated in vacuo to provide crude 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-ol (257 mg, 0.535 mmol, 97% yield) which was used without further purification. MS: [M+H]+ m/z 480.

Workup

  1. customdried 20 mL microwave vial
  2. additioncharged with THF (10 ml)
  3. customdegassed under nitrogen
  4. temperaturethe reaction was slowly warmed to rt over 30 minutes
  5. customThe reaction was quenched with saturated ammonium chloride
  6. extractionextracted 3×20 mL EtOAc
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18f069a3a4ef40bc8097d721828d2a5a
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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