2-Fluoro-4-nitrophenol → 1-(1-Ethyl-4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-2-yl)-N,N-dimethylmethanamine

HRID 2193700Notes

Reaction equation

HRID 2193700 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[C:13]([CH2:18][N:19]([CH3:21])[CH3:20])[N:14]([CH2:16][CH3:17])[CH:15]=3)[S:10][C:3]=12.[F:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[OH:32].C(N1C=C(C2SC3C(=NC=CC=3OC3C=CC([N+]([O-])=O)=CC=3F)C=2)N=C1)C>>[CH2:16]([N:14]1[CH:15]=[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:32][C:24]3[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:23]=3[F:22])[CH:8]=2)[N:12]=[C:13]1[CH2:18][N:19]([CH3:21])[CH3:20])[CH3:17]

Participants

4

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 587902451-(4-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-ethyl-1H-imidazol-2-yl)-N,N-dimethylmethanamineHCID 666490322-(1-Ethyl-1H-imidazol-4-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 587904001-(1-Ethyl-4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-2-yl)-N,N-dimethylmethanamineYield 48%

Procedure

Starting from the chloride 112 and 2-fluoro-4-nitrophenol and following the same procedure as described above for the synthesis of compound 14 (scheme 4), title compound 113 was obtained as yellow solid in 48% yield. MS (m/z): 442.1 (M+H).

Sources & evidence

ORD record
ord-6e9dfcba1d4c405ab9cafed467f1c8b7
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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