Potassium Phosphate, Tribasic → 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634106Notes

Reaction equation

HRID 634106 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[Cl:36][C:37]1[N:42]=[C:41](B(O)O)[CH:40]=[CH:39][CH:38]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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>[Cl:36][C:37]1[N:42]=[C:41]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[O:15][C:14]([NH:16][CH2:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=5)=[N:13][N:12]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:3]=2)[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 228320876-Chloropyridine-2-boronic acidHCID 683283255-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 867250945-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amineYield 53.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To the solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (1.0 g, 1.66 mmol) and 6-chloropyridin-2-ylboronic acid (0.392 g, 2.49 mmol) in DMF (10 mL) was added K3PO4 (0.704 g, 3.32 mmol) and this solution was purged under N2 for 15 min. Then Pd(PPh3)4 (0.176 g, 0.152 mmol) was added and the reaction was heated at 85° C. for 5 h. The solution was poured in ice cold water (50 mL) and extracted with EtOAc. The combined organic layers were washed with H2O, dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 15% EtOAc in Hex) to give 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.52 g, 53.3%) as a brown solid. MS (ESI, pos. ion) m/z: 586 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ ppm 8.94 (s, 1H), 8.79 (s, 1H), 8.16-8.14 (m, 2H), 8.03-7.97 (m, 4H), 7.67-7.55 (m, 1H), 7.49-7.42 (m, 3H), 7.34 (d, J=8.4 Hz, 2H), 6.9 (d, J=8.1 Hz, 2H), 4.38 (s, 2H), 3.72 (s, 3H), 2.32 (s, 3H).

Workup

  1. customthis solution was purged under N2 for 15 min
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (eluting with 15% EtOAc in Hex)

Sources & evidence

ORD record
ord-57a2692486c34403a7b6b8af32718698
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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