tert-Butyl carbamate → tert-butyl (3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

HRID 571376Notes

Reaction equation

HRID 571376 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[C:37](=[O:44])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[NH2:38].CC(C)([O-])C.[K+]>C1COCC1>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:8]2[C:5]3[CH:6]=[N:7][C:2]([NH:38][C:37](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:3][C:4]=3[N:10]([C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 77922tert-Butyl carbamateHCID 23665647Potassium tert-butoxideHCID 895258266-chloro-3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 117621990tert-butyl (3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamateYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.48 g, 3.02 mmol), tert-butyl carbamate (1.062 g, 9.06 mmol), and chloro(2-di-t-butylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) (0.249 g, 0.362 mmol) was dissolved in THF (30 mL) then potassium tert-butoxide (6.65 mL, 6.65 mmol, 1 M in THF) was added. The reaction mixture was purged under argon for five minutes then heated to 80° C. and stirred overnight. The reaction mixture was diluted with DCM and washed with NaOH (1 N) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo while loading onto silica gel. The residue was purified by flash chromatography (2-20% EtOAc/isohexane) to give tert-butyl (3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (403 mg, 0.706 mmol, 23%). MS ESI calc'd. For C36H31FN4O2 [M+1]+ 571, found 571.

Workup

  1. customThe reaction mixture was purged under argon for five minutes
  2. additionThe reaction mixture was diluted with DCM
  3. washwashed with NaOH (1 N) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (2-20% EtOAc/isohexane)

Sources & evidence

ORD record
ord-5b44492f3b31437c98738d9d01c1988e
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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