6-Bromo-3-methyl-1,2-benzoxazole → N-[4-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)phenyl]thiophene-3-carboxamide

HRID 1988913Notes

Reaction equation

HRID 1988913 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.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)=[O:21])=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1>>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)=[O:21])=[CH:17][C:18]=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 21914662N-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-thiophenecarboxamide2×

Product 1

HCID 10450424N-[4-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)phenyl]thiophene-3-carboxamideYield 49.3%

Procedure

Example 5 was prepared in a similar manner to Example 4 using 6-bromo-3-methyl-1,2-benzisoxazole (11 mg) and N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-thiopheneamide (Intermediate 15, 17 mg) to give an oil (8.5 mg).

Sources & evidence

ORD record
ord-616b354f8f0c425ea046b94f7471e7ec
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…