Triethylamine → 4-Fluoro-N-[3-(furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]benzamide

HRID 1991122Notes

Reaction equation

HRID 1991122 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[O:11]1[CH:15]=[CH:14][C:13]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([NH2:25])[CH:23]=3)[NH:18][CH:17]=2)=[CH:12]1.CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:25][C:22]2[CH:23]=[C:24]3[C:16]([C:13]4[CH:14]=[CH:15][O:11][CH:12]=4)=[CH:17][NH:18][C:19]3=[N:20][CH:21]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 160643543-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Product 1

HCID 160643504-Fluoro-N-[3-(furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]benzamideYield 5.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Fluorobenzoyl chloride (29.7 mg, 0.19 mmol) was added to a solution of amine 48 (25 mg, 0.125 mmol), DMAP (1.53 mg, 12.5 μmol) and Et3N (12.6 mg, 0.125 mmol) in DMF (0.6 mL). The mixture was stirred at r.t. overnight, concentrated and separated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 49 (2.13 mg, 5%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 6.45 (dd, J=1.9, 0.9 Hz, 1H), 6.91 (t, J=1.8 Hz, 2H), 7.22 (s, 1H), 7.23 (t, J=1.7 Hz, 1H), 7.56 (m, 1H), 7.73-7.76 (m, 2H), 8.15 (d, J=2.1 Hz, 1H), 8.25 (d, J=2.3 Hz, 1H); MS (ES) m/z 363 (MH++MeCN).

Workup

  1. concentrationconcentrated
  2. customseparated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-82329cac2f2745a79682e7617d8d85e3
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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