3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

HRID 1180268Notes

Reaction equation

HRID 1180268 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[F:23]>>[Cl:16][C:17]1[CH:18]=[C:19]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]3=[N:4][CH:3]=2)[CH:20]=[CH:21][C:22]=1[F:23]

Participants

3

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 674866802-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-olYield 85%

Procedure

2-(3-Bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol and 3-chloro-4-fluorobenzeneboronic acid were coupled together as described in Example 1 to give 2-[3-(3-chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]propan-2-ol as a white solid (7.10 g, 85%): δH (400 MHz, CDCl3) 1.74 (6H, s), 2.08 (1H, s), 7.21 (1H, t, J 7), 7.31 (1H, t, J 9), 7.40-7.44 (1H, m), 7.60 (1H, dd, J 7 and 2), 7.67 (1H, s), 8.01 (1H, d, J 7); m/z (ES+) 323 [MH+].

Sources & evidence

ORD record
ord-c2b5447f54aa416d9cc4ac9752bed3a2
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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