N2-(4-bromophenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine → (5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

HRID 897932Notes

Reaction equation

HRID 897932 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][C:11]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.FC1C=C([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)C=CC=1NC1OC2C=CC=CC=2N=1>>[CH3:34][C:29]1([CH3:35])[C:30]([CH3:33])([CH3:32])[O:31][B:27]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]3[O:10][C:11]4[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:12]=4[N:13]=3)=[CH:4][CH:3]=2)[O:28]1

Participants

3

Reactant 2

HCID 22346792N2-(4-bromophenyl)-5,7-dimethyl-1,3-benzoxazol-2-amineHCID 22347094N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazol-2-amine

Product 1

HCID 11581347(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

Procedure

N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5,7-dimethyl-1,3-benzoxazol-2-amine was prepared from N2-(4-bromophenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine (1.215 g, 3.831 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 tan powder (0.880 g, 63%). 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=14.48 min, 81%; m/z 365 (MH+).

Sources & evidence

ORD record
ord-06fc83737d59492297f58de903a146a3
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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