6-Bromo-3-methyl-1,2-benzoxazole → 4-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)-N-(1,3-thiazol-2-yl)benzamide

HRID 1988916Notes

Reaction equation

HRID 1988916 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[NH:17][C:18](=[O:35])[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=1>>[CH3:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([NH:17][C:13]2[S:12][CH:16]=[CH:15][N:14]=2)=[O:35])=[CH:24][C:23]=1[C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 124113226-Bromo-3-methyl-1,2-benzoxazoleHCID 219145174-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide2×

Product 1

HCID 104504804-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)-N-(1,3-thiazol-2-yl)benzamideYield 7.5%

Procedure

Example 8 was prepared in a similar manner to Example 4 using 6-bromo-3-methyl-1,2-benzisoxazole (11 mg) and N-(thiazol-2-yl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 18, 17 mg) followed by purification via mass directed autoprep to give the title compound as an oil (1.3 mg).

Workup

  1. customfollowed by purification via mass

Sources & evidence

ORD record
ord-04faeb0a5c8d4c938864c4c53e59ddbb
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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