2-(4-Bromophenyl)imidazo[1,2-a]pyridine → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)imidazo[1,2-a]pyridine

HRID 897939Notes

Reaction equation

HRID 897939 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[CH:16]=2)=[CH:4][CH:3]=1.FC1C=C([B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)C=CC=1NC1OC2C=CC=CC=2N=1>>[CH3:31][C:26]1([CH3:32])[C:27]([CH3:30])([CH3:29])[O:28][B:24]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][N:11]4[CH:16]=3)=[CH:4][CH:3]=2)[O:25]1

Participants

3

Reactant 2

HCID 6234162-(4-Bromophenyl)imidazo[1,2-a]pyridineHCID 22347094N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazol-2-amine

Product 1

HCID 223467412-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)imidazo[1,2-a]pyridine

Procedure

2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyridine was prepared from 2-(4-bromophenyl)imidazo[1,2-a]pyridine (0.273 g, 1.00 mmol) in a manner similar to that used for the preparation of N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazol-2-amine. The compound was formed as a white solid (0.250 g, 78%). RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) Rt=11.35 min, 87%; m/z 321 (MH+).

Sources & evidence

ORD record
ord-0d03a8768f1f4724aae07fe34f6ec77e
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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