Chloride → 3-Bromo-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-5-yl)benzonitrile
Reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[Br:19])[CH:8]=[N:7][CH:6]=1.[Cl-].CC([O-])(C)C.[K+]>>[Br:19][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:11]=1[CH:10]1[N:9]2[CH:8]=[N:7][CH:6]=[C:5]2[CH2:4][CH2:3][CH2:2]1)[C:15]#[N:16]Participants
4
Procedure
4-{5-[3-Hydroxypropyl]imidazol-1-ylmethyl}-3-bromobenzonitrile is converted to the corresponding chloride according to Example 14B. The resulting chloride is treated with a base, such as t-BuOK as in Example 14C above, to effect cyclization to the title compound. MS (ESI) m/z 302.1, 304.1 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.74-1.85 (m, 2H), 2.08-2.17 (m, 1H), 2.34-2.43 (m, 1H), 2.82-2.91 (m, 1H), 2.93-3.00 (m, 1H), 5.88 (t, J=5.6 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 6.82 (d, J=1.0 Hz, 1H), 7.34 (s, 1H), 7.69 (dd, J=8.1, 1.5 Hz, 1H), 8.09 (d, J=1.5 Hz, 1H).
Sources & evidence
- ORD record
- ord-adcfa5beae544d0e9e786f2fa062abf6
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835646B2
Reaction notes
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