Potassium benzyltrifluoroboranuide → 3-Benzyl-10-bromo-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575140Notes

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.[CH2:21]([B-](F)(F)F)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[K+]>>[CH2:21]([C:12]1[N:8]2[CH2:9][CH2:10][O:11][C:5]3[CH:4]=[C:3]([F:20])[C:2]([Br:1])=[CH:19][C:6]=3[C:7]2=[N:14][C:13]=1[C:15]([NH2:17])=[O:16])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Reactant 2

HCID 23692459Potassium benzyltrifluoroboranuide

HCID 8669305210-Bromo-9-fluoro-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 897551113-Benzyl-10-bromo-9-fluoro-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 (70 mg) was reacted with potassium benzyltrifluoroborate similar to as described in Example 5 and purified by reverse phase hplc to give 3-benzyl-10-bromo-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide. This intermediate was reacted with 2-Methyl-3-butyne-ol similar to as described in Procedure E to afford 4.9 mg of 3-benzyl-9-fluoro-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) 420 (M)+. 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=8.2 Hz, 1H), 7.28 (d, J=7.1 Hz, 1H), 7.22-7.15 (m, 3H), 6.69 (d, J=9.9 Hz, 1H), 5.46 (s, 1H), 4.59 (s, 2H), 4.31 (dd, J=5.2, 3.1 Hz, 2H), 4.04 (dd, J=5.1, 3.1 Hz, 2H), 1.65 (s, 6H).

Workup

custompurified by reverse phase

Sources & evidence

ORD record: ord-7c7595956efa4e4294006ca8f3440746
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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