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

HRID 1988915Notes

Reaction equation

HRID 1988915 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:33]=[CH:32][C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:21]=2)=[O:18])=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1>>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:21]=2)=[O:18])=[CH:32][C:33]=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 597915214-methyl-N-[3-(4-morpholinyl)phenyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide2×

Product 1

HCID 104326764-Methyl-3-(3-methyl-1,2-benzisoxazol-6-yl)-N-(3-morpholin-4-ylphenyl)benzamideYield 45.2%

Procedure

Example 7 was prepared in a similar manner to Example 4 using 6-bromo-3-methyl-1,2-benzisoxazole (11 mg) and 4-methyl-N-(3-morpholin-4-yl-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 9, 21 mg) to give the title compound as an oil (9.6 mg).

Sources & evidence

ORD record
ord-d443d8c7b4824d348053dc4c42e66a17
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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