1H-Indole-2-carboxylic acid, 1-methyl- → N-[4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-1-methylindole-2-carboxamide

HRID 1634108Notes

Reaction equation

HRID 1634108 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([CH2:12][CH3:13])[N:9]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[C:31](O)=[O:32].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:12]([C:10]1[N:9]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:31]([C:23]3[N:22]([CH3:21])[C:30]4[C:25]([CH:24]=3)=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:32])=[CH:18][CH:19]=2)[N:8]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:11]=1)[CH3:13]

Participants

6

Reactant 4

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 186770941-(4-Aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole

Product 1

HCID 9888438N-[4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-1-methylindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF (2 mL) solution of 3-(3-pyridyl)-5-ethyl-1-(4′-aminophenyl)pyrazole (264 mg, 1 mmol), N-methylindole-2-carboxylic acid (192.5 mg, 1.1 mmol), PyBOP (570 mg, 1.1 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) was stirred at room temperature. for 18 hr. The reaction mixture was poured into crushed ice, and extracted with methylene chloride (3×50 mL). The combined extracts were washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. Chromatography of the residue over silica gel (4% methanol/methylene chloride) followed by preparative TLC (silica gel, developer 5% methanol/methylene chloride) gave the title compound as a light, cream colored solid, m.p. 178-179° C. 1H NMR (DMSO-d6) δ 1.2 (3H, t, J=7.5), 2.73 (2H, q, J=7.5 Hz), 4.05 (3H, s), 6.93 (1H, s), 7.16 (1H, t, J=7.5), 7.34 (1H, t, J=7.5), 7.37 (1H, s), 7.44-7.48 (1H, dd, J=3.1 & 4.7 Hz), 7.57-7.61 (3H, m), 7.74 (1H, d, J=7.9 Hz), 7.98 (2H, d, J=8.8 Hz), 8.2-8.22 (1H, m), 8.53-8.54 (1H, m), 9.07 (1H, d, J=1.8 Hz), 10.56 (1H, s).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. extractionextracted with methylene chloride (3×50 mL)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4bf5762168df4621b56e01dfd651de67
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…