4-Bromoaniline → N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide

HRID 715768Notes

Reaction equation

HRID 715768 reaction equation
C(N1C=C(B2O[C:13](C)(C)[C:12](C)([CH3:17])[O:11]2)C=N1)C(C)C.Br[C:20]1[S:24][C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][N:32]3[CH:35]=[CH:36][N:37]=[C:31]3[CH:30]=2)=[O:26])=[CH:22][CH:21]=1.Br[C:39]1[CH:45]=[CH:44][C:42](N)=[CH:41][CH:40]=1>>[N:37]1[CH:36]=[CH:35][N:32]2[CH:33]=[CH:34][C:29]([CH2:28][NH:27][C:25]([C:23]3[S:24][C:20]([C:41]4[CH:42]=[CH:44][CH:45]=[C:39]([O:11][CH:12]([CH3:17])[CH3:13])[CH:40]=4)=[CH:21][CH:22]=3)=[O:26])=[CH:30][C:31]=12

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867019355-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide

Product 1

HCID 86701941N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide

Procedure

The title compound was prepared as described in Example 51A, substituting 2-(3-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 8.19 (d, J=0.4 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.86 (d, J=0.5 Hz, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.24 (d, J=3.9 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 4.13 (d, J=6.6 Hz, 2H), 3.09-2.83 (m, 4H), 2.47-2.40 (m, 1H), 2.14-1.96 (m, 1H), 1.88-1.69 (m, 1H), 1.69-1.54 (m, 1H), 1.37-1.14 (m, 1H).

Sources & evidence

ORD record
ord-6720e22bdb65410d9ff0191cd02510f4
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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