Acetonitrile → N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-ynamide

HRID 1500827Notes

Reaction equation

HRID 1500827 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=3)[NH2:14])[CH:9]=2)[NH:4][CH:3]=1.C(N([CH2:23][CH3:24])CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)[O:29]1)CC.[C:43](#N)[CH3:44]>C(OCC)(=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:14][C:43](=[O:29])[C:44]#[C:23][CH3:24])[CH:15]=[CH:16][CH:17]=3)[CH:9]=2)[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1176525073-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline

Product 1

HCID 86301779N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-ynamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 24 (25 mg, 0.112 mmol) and 55 (9.4 mg, 0.112 mmol) in acetonitrile (4 mL) was added triethylamine (22.6 mg, 0.224 mmol). T3P (71.27 mg, 0.224 mmol) was added to the reaction mixture. The reaction was stirred overnight at rt. The reaction was diluted with ethyl acetate (25 mL). The organic layer was washed with water (25 mL) followed by brine solution (25 mL). The organic layer was dried over sodium sulphate, filtered and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 1.5% methanol in chloroform as pale yellow colour solid compound 63. MS-ES+289.9; 1H NMR (400 MHz, DMSO-D6): 11.38 (s, 1H), 10.68 (s, 1H), 8.41 (s, 1H), 8.07 (s, 1H), 7.91 (s, 1H), 7.58 (m, 1H), 7.40 (m, 2H), 7.28 (s, 1H), 2.30 (s, 3H), 2.06 (s, 3H).

Workup

  1. washThe organic layer was washed with water (25 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto get the crude, which
  6. customwas purified through flash chromatography
  7. washThe compound was eluted at 1.5% methanol in chloroform as pale yellow colour solid compound 63

Sources & evidence

ORD record
ord-fae2c2b0635942ae8cc508f672b34584
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

Loading…