N-(4-Bromophenyl)benzo[d]thiazol-2-amine → N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]thiazol-2-amine

HRID 432383Notes

Reaction equation

HRID 432383 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.FC1C=C([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)C=CC=1NC1OC2C=CC=CC=2N=1>>[CH3:32][C:27]1([CH3:33])[C:28]([CH3:31])([CH3:30])[O:29][B:25]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)=[CH:4][CH:3]=2)[O:26]1

Participants

3

Reactant 2

HCID 234496N-(4-Bromophenyl)benzo[d]thiazol-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 22347024N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]thiazol-2-amine

Procedure

N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazol-2-amine was prepared from N2-(4-bromophenyl)-1,3-benzothiazol-2-amine (0.909 g, 2.98 mmol) in a manner similar to that used for 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 an off-white powder (0.321 g, 31%). 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) tr=13.82 min., 92%; m/z 351 (MH+).

Sources & evidence

ORD record
ord-f0cb90423db747c099efacf08702ee8c
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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