Potassium Trifluoro(methyl)borate → 10-Bromo-9-fluoro-3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575142Notes

Reaction equation

HRID 575142 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12](I)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1.[CH3:21][B-](F)(F)F.[K+]>>[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH3:21])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1

Participants

3

Reactant 2

HCID 23692566Potassium Trifluoro(methyl)borateHCID 8669305210-Bromo-9-fluoro-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8975468510-Bromo-9-fluoro-3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Procedure

10-Bromo-9-fluoro-3-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide (0.2 g) was reacted with potassium methyltrifluoroborate similar to as described in Example 5 to give 20 mg of 10-bromo-9-fluoro-3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide after reverse phase hplc purification. This intermediate was reacted with 2-Methyl-3-butyne-ol similar to as described in Procedure E to afford 17.4 mg of 9-fluoro-3-[(2-fluorophenyl)methyl]-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide following reverse phase hplc purification. MS (Q1) 344 (M)+. 1H NMR (400 MHz, DMSO) δ 8.55 (dd, J=8.5, 3.5 Hz, 1H), 7.48 (s, 1H), 6.98 (d, J=10.5 Hz, 2H), 5.49 (s, 1H), 4.63-4.36 (m, 2H), 4.35-4.24 (m, 2H), 1.49 (s, 6H).

Sources & evidence

ORD record
ord-107a6b6e55694ed58ef0ea03dcdb92ba
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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