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

HRID 1500828Notes

Reaction equation

HRID 1500828 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(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP([CH2:39][CH2:40][CH3:41])(=O)O1)CC.[C:43](OCC)(=[O:45])[CH3:44]>C(#N)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:45])[C:44]#[C:39][CH2:40][CH3:41])[CH:15]=[CH:16][CH:17]=3)[CH:9]=2)[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 111923Propylphosphonic anhydrideHCID 1176525073-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline

Product 1

HCID 86301781N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)pent-2-ynamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 24 (25 mg, 0.112 mmol) and 59 (9.86 mg, 0.112 mmol) in acetonitrile (4 mL) was added triethylamine (22.6 mg, 0.224 mmol). T3P (71.1 mg, 0.224 mmol) was added to the reaction mixture. The reaction was stirred overnight at rt, then 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 2% methanol in chloroform as pale yellow colour solid compound 64. MS-ES+303.9; 1H NMR (400 MHz, DMSO-D6) 64: 11.37 (s, 1H), 10.65 (s, 1H), 8.41 (d, 1H), 8.06 (d, 1H), 7.90 (bs, 1H), 7.59 (d, 1H), 7.40 (m, 2H), 7.28 (bs, 1H), 2.42 (m, 2H), 2.30 (bs, 3H), 1.17 (t, 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 2% methanol in chloroform as pale yellow colour solid compound 64

Sources & evidence

ORD record
ord-acdec813792047669f11d7fa8a873105
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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