4-(Bromomethyl)-2-chloropyridine → 4-(bromomethyl)-ethyl-1H-pyrrolo[2,3-b]pyridine
Reaction equation
O[CH2:2][C:3]1[N:8]=[CH:7][C:6](CC2C=C3C(=C4C=CC=CC=24)N=CN([C@H]2CCOC[C@@H]2O)C3=O)=CC=1.[Br:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36](Cl)[CH:35]=1>>[Br:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]2[N:8]([CH2:3][CH3:2])[CH:7]=[CH:6][C:35]=12Participants
Procedure
The title compound was prepared by the procedure described for the synthesis of 6-[(2-chloropyridin-4-yl)methyl]-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3R)-one in Example 15, substituting 4-(bromomethyl)-1-ethyl-1H-pyrrolo[2,3-b]pyridine for 4-(bromomethyl)-2-chloropyridine. The resultant orange solid gave proton NMR spectra consistent with theory and a mass ion (ES+) of 455.2087 for [M+H]+ [Calc'd for C27H27N4O3, [M+H]+=455.2078]: 1H NMR (400 MHz, d6-DMSO) δ 9.01-8.98 (m, 1H), 8.71 (s, 1H), 8.14-8.08 (m, 2H), 8.01 (s, 1H), 7.75-7.71 (m, 2H), 7.56 (s, 1H), 6.74-6.72 (m, 1H), 6.59 (s, 1H), 5.31 (d, J=5.5 Hz, 1H), 4.80 (s, 2H), 4.63 (br s, 1H), 4.28 (q, J=7.2 Hz, 2H), 4.18-4.15 (m, 1H), 3.99-3.92 (m, 1H), 3.42 (t, J=11.1 Hz, 1H), 3.14 (t, J=10.4 Hz, 1H), 2.26 (br s, 1H), 1.91-1.89 (m, 1H), 1.38 (t, J=7.2 Hz, 3H).
Workup
- customThe resultant orange solid gave proton NMR spectra consistent with theory
Sources & evidence
- ORD record
- ord-5620b28da73e42368d676694dab7aac3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846702B2
Reaction notes
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