(Pyridin-4-yl)boronic acid → 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid

HRID 1467326Notes

Reaction equation

HRID 1467326 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[N:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>>[N:33]1[CH:38]=[CH:37][C:36]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=3)[N:4]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 679965973-bromo-1-trityl-1H-indazole-5-carboxylic acid

Product 1

HCID 679963353-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid

Conditions

Temperature
80 °C

Procedure

3-bromo-1-trityl-1H-indazole-5-carboxylic acid (500 mg, 1.04 mol) was added to a vial containing pyridin-4-ylboronic acid (128 mg, 1.04 mol) and tetrakis(triphenyl-phosphine)palladium (120 mg, 0.104 mol). After purging the vial with nitrogen gas, dioxane (5 mL) and 2M sodium carbonate (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 (30 mL) was added and pH was adjusted to 7 by HCl. The mixture was extracted using dichloromethane (3×100 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using prep LC/MS.

Workup

  1. customAfter purging the vial with nitrogen gas, dioxane (5 mL) and 2M sodium carbonate (5 mL)
  2. additionwas added to the vial respectively
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. additionWater (30 mL) was added
  5. extractionThe mixture was extracted
  6. customdried
  7. filtrationThe resulting suspension was filtered
  8. concentrationconcentrated
  9. customThe crude product was purified

Sources & evidence

ORD record
ord-a92c1fa68258492daf7a73b6d379792b
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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