4-Bromo-3-fluorotoluene → 2-(2-Fluoro-4-methylphenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine

HRID 1177409Notes

Reaction equation

HRID 1177409 reaction equation
BrC1C=CC(C)=CC=1F.ClC1C(N=C=S)=CC=C(Cl)N=1.O1CCCO[CH:22]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[S:34][C:35]3[C:40]([N:41]=2)=[CH:39][CH:38]=[C:37]([C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH2:43])[N:36]=3)=[C:29]([F:50])[CH:28]=1>>[F:50][C:29]1[CH:28]=[C:27]([CH3:22])[CH:32]=[CH:31][C:30]=1[C:33]1[S:34][C:35]2[C:40]([N:41]=1)=[CH:39][CH:38]=[C:37]([C:42]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[CH2:43])[N:36]=2

Participants

4

Reactant 3

HCID 5732804-Bromo-3-fluorotolueneHCID 671118192-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridineHCID 715192602,6-Dichloro-3-isothiocyanatopyridine

Product 1

HCID 591748892-(2-Fluoro-4-methylphenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine

Procedure

Synthesized from 1-bromo-2-fluoro-4-methylbenzene (10 g, 53 mmol) and 2,6-dichloro-3-isothiocyanatopyridine (11 g, 53 mmol) according to the procedure for the synthesis of intermediate (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)-thiazolo[5,4-b]pyridine) to give 2-(2-fluoro-4-methylphenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine as a tan solid. MS (ESI) m/z: calculated: 346.1; Observed: 347.1 (M++1).

Sources & evidence

ORD record
ord-8c325f4cf557480f8184b860c0c83fcc
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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