N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2-pyrrolidin-1-yl-isonicotinamide → N-(4-methyl-3-(3-methylbenzo[d]isoxazol-5-yl)phenyl)-2-(pyrrolidin-1-yl)isonicotinamide

HRID 1988917Notes

Reaction equation

HRID 1988917 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:22]=2)=[CH:15][C:14]=1B1OC(C)(C)C(C)(C)O1>>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:22]=2)=[CH:15][C:14]=1[C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1

Participants

3

Reactant 2

HCID 11258289N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2-pyrrolidin-1-yl-isonicotinamide2×HCID 124113305-Bromo-3-methyl-1,2-benzoxazole

Product 1

HCID 44580730N-(4-methyl-3-(3-methylbenzo[d]isoxazol-5-yl)phenyl)-2-(pyrrolidin-1-yl)isonicotinamide

Procedure

Example 10 was prepared in a similar manner to Example 4 using 5-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]-2-pyrrolidin-1-yl-isonicotinamide (Intermediate 13, 16 mg) to give the title compound as an oil (6.6).

Sources & evidence

ORD record
ord-3a9c6aa6580844dbbcc88f5314371011
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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