5-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride) → 2-(5-Bromo-thiophen-2-yl)-4-(3,4-dichlorophenyl)-6-methyl-pyridine

HRID 1927942Notes

Reaction equation

HRID 1927942 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11](I)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:17][C:18]1[S:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[Br:17][C:18]1[S:22][C:21]([C:11]2[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH:14]=[C:13]([CH3:15])[N:12]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27343195-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride)HCID 574686764-(3,4-Dichloro-phenyl)-2-iodo-6-methylpyridine

Product 1

HCID 574688012-(5-Bromo-thiophen-2-yl)-4-(3,4-dichlorophenyl)-6-methyl-pyridine

Procedure

The title compound was prepared from 4-(3,4-dichloro-phenyl)-2-iodo-6-methyl-pyridine (example A.52) (1.0 g, ca. 80% pure, ca. 2.75 mmol) and commercially available 5-bromthiophene-2-boronic acid (0.568 g, 2.75 mmol) according to the general procedure IVb. Obtained as an off-white solid (0.480 g, 46%). MS (ISP) 397.9 [(M+H)+], 400.0 [(M+2+H)+], 402.1 [(M+4+H)+] and 404.2 [(M+6+H)+].

Sources & evidence

ORD record
ord-e8a95888510643949223353396dba9cb
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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