Potassium Carbonate → HCID 49803865, compound

HRID 384974Notes

Reaction equation

HRID 384974 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:18])[C:12]1=[O:26].[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>O.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:26]=[C:12]1[C:13]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[O:18])=[CH:14][CH:15]=[CH:16][N:11]1[CH:6]1[C:7]2[C:3](=[C:2]([C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 49800430HCID 49800430, compound

Product 1

HCID 49803865HCID 49803865, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

2-oxo-1-(4-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-yl)-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide was prepared by heating a mixture of 1-(4-bromo-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (35.1 mg, 0.0855 mmol, 1.0 eq.), pyridin-3-ylboronic acid (12.8 mg, 0.104 mmol, 1.2 eq.), Pd(PPh3)4 (5.6 mg, 0.0048 mmol, 0.056 eq.), and potassium carbonate (15.1 mg, 0.109 mmol, 1.3 eq.) in 0.80 mL of dioxanes and 0.20 mL of H2O in a microwave at 140° C. for 5 min. The crude material was filtered through celite and the filtrate was purified by reverse phase HPLC using the method of 5-35% ACN/H2O in 40 min The purified material was concentrated and dried under vacuum to give 2-oxo-1-(4-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-yl)-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide as a clear colorless oil. Retention time (min)=8.051, method [8], MS (ESI) 409.2 (M+H); 1H NMR (300 MHz, CDCl3) δ 9.19 (m, 1H), 8.90 (m, 1H), 8.67 (m, 2H), 8.53 (m, 2H), 8.24 (d, J=7.1 Hz, 2H), 8.06 (m, 1H), 7.53 (m, 2H), 7.32 (m, 1H), 6.71 (t, J=7.7 Hz, 1H), 6.62 (t, J=7.1 Hz, 1H), 3.20 (m, 3H), 2.95 (m 1H), 2.19 (m, 1H).

Workup

  1. custom2-oxo-1-(4-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-yl)-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide was prepared
  2. temperatureby heating
  3. filtrationThe crude material was filtered through celite
  4. customthe filtrate was purified by reverse phase HPLC
  5. customin 40 min
  6. concentrationwas concentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-79a71490d5fb4587a49ae6b3dbe610df
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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