(Pyridin-4-yl)boronic acid → tert-butyl 4-(3-fluorophenyl)-3-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

HRID 1467321Notes

Reaction equation

HRID 1467321 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][CH:14]3[CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)[CH2:18][CH2:17][N:16]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:3]=1.[N:53]1[CH:58]=[CH:57][C:56](B(O)O)=[CH:55][CH:54]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:26][C:22]1[CH:21]=[C:20]([CH:19]2[CH2:18][CH2:17][N:16]([C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[CH2:15][CH:14]2[NH:13][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:3]=[C:2]3[C:56]2[CH:57]=[CH:58][N:53]=[CH:54][CH:55]=2)=[O:12])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 67996835tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)-4-(3-fluorophenyl)piperidine-1-carboxylate

Product 1

HCID 67996977tert-butyl 4-(3-fluorophenyl)-3-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)-4-(3-fluorophenyl)-piperidine-1-carboxylate (80 mg, 0.105 mmol) was added to a vial containing pyridin-4-ylboronic acid (13 mg, 0.105 mmol) and tetrakis(triphenylphosphine)palladium (13 mg, 0.0105 mmol). After purging the vial with nitrogen gas, dioxane (0.5 mL) and 2M sodium carbonate (0.5 mL) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for overnight. Upon completion, the mixture was concentrated under vacuo. Water (3 mL) was added and was extracted using dichloromethane (3×5 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was progressed to the next step without purification.

Workup

  1. customAfter purging the vial with nitrogen gas, dioxane (0.5 mL) and 2M sodium carbonate (0.5 mL)
  2. additionwas added to the vial respectively
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. additionWater (3 mL) was added
  5. extractionwas extracted
  6. customdried
  7. filtrationThe resulting suspension was filtered
  8. concentrationconcentrated
  9. customThe crude product was progressed to the next step without purification

Sources & evidence

ORD record
ord-93b8ce6e91fc40dfb369978dbceaf674
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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