(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → (R)-tert-butyl 3-(3-(2,3-dihydrobenzofuran-5-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

HRID 1467333Notes

Reaction equation

HRID 1467333 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.[O:46]1[C:50]2[CH:51]=[CH:52][C:53](B(O)O)=[CH:54][C:49]=2[CH2:48][CH2:47]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>[O:46]1[C:50]2[CH:51]=[CH:52][C:53]([C:2]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]5[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]5)=[O:12])[CH:9]=4)[N:4]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:3]=3)=[CH:54][C:49]=2[CH2:48][CH2:47]1

Participants

4

Reactant 2

HCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 70652333(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Product 1

HCID 67997292(R)-tert-butyl 3-(3-(2,3-dihydrobenzofuran-5-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate (650 mg, 1 mmol) was added to a vial containing 2,3-dihydrobenzofuran-5-ylboronic acid (180 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol). After purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 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 (10 mL) was added and was extracted using dichloromethane (3×25 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using flash chromatography.

Workup

  1. customAfter purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 mL)
  2. additionwas added to the vial respectively
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. additionWater (10 mL) was added
  5. extractionwas extracted
  6. customdried
  7. filtrationThe resulting suspension was filtered
  8. concentrationconcentrated
  9. customThe crude product was purified

Sources & evidence

ORD record
ord-3d32aefa722d46a3a02248cbf0461f8c
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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