N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine → N2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-methyl-1,3-benzoxazol-2-amine

HRID 897918Notes

Reaction equation

HRID 897918 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH3:19][C:20]1([CH3:44])[C:24]([CH3:26])([CH3:25])[O:23][B:22](C2C=CC(NC3OC4C=CC(Cl)=CC=4N=3)=CC=2)[O:21]1>>[CH3:19][C:20]1([CH3:44])[C:24]([CH3:26])([CH3:25])[O:23][B:22]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]3[O:10][C:11]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:12]=4[N:13]=3)=[CH:4][CH:3]=2)[O:21]1

Participants

3

Reactant 2

HCID 21985825N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amineHCID 22346666N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine

Product 1

HCID 22347264N2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-methyl-1,3-benzoxazol-2-amine

Procedure

N2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-methyl-1,3-benzoxazol-2-amine was prepared from N2-(4-bromophenyl)-5-methyl-1,3-benzoxazol-2-amine (1.5 g, 4.95 mmol) using the method described for the preparation of N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine. The product was formed as white floculent solid (0.79 g, 46%); RP-HPLC Rt 17.382 min, 98% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); 1H NMR (400 MHz, d6-DMSO) 1.29 (12H, s), 2.38 (3H, s), 6.94 (1H, d, J 8.1 Hz), 7.30 (1H, s), 7.36 (1H, d, J 8.1 Hz), 7.67 (2H, d, J 8.5 Hz), 7.75 (2H, d, J 8.5 Hz), and 10.74 (1H, s).

Sources & evidence

ORD record
ord-555eabb2a2d64458aaa1749bf59d1f05
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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