Benzonitrile, 4-bromo- → 3'-((R)-3-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-5-yl)-4'-fluoro-biphenyl-4-carbonitrile

HRID 331158Notes

Reaction equation

HRID 331158 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:24][C:25]2[CH2:26][O:27][C:28]([CH3:51])([CH3:50])[C:29]([F:49])([F:48])[C@:30]([C:33]3[CH:38]=[C:37](B4OCC(C)(C)CO4)[CH:36]=[CH:35][C:34]=3[F:47])([CH3:32])[N:31]=2)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Br[C:53]1[CH:60]=[CH:59][C:56]([C:57]#[N:58])=[CH:55][CH:54]=1>>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:9]([NH:24][C:25]2[CH2:26][O:27][C:28]([CH3:50])([CH3:51])[C:29]([F:48])([F:49])[C@:30]([C:33]3[CH:38]=[C:37]([C:53]4[CH:60]=[CH:59][C:56]([C:57]#[N:58])=[CH:55][CH:54]=4)[CH:36]=[CH:35][C:34]=3[F:47])([CH3:32])[N:31]=2)([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 12162Benzonitrile, 4-bromo-HCID 68380558[bis-(4-methoxy-phenyl)-phenyl-methyl]-{(R)-5-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl}-amine

Product 1

HCID 683805433'-((R)-3-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-5-yl)-4'-fluoro-biphenyl-4-carbonitrileYield 78.2%

Procedure

Reaction of [bis-(4-methoxy-phenyl)-phenyl-methyl]-{(R)-5-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl}-amine (intermediate B10.1) (199 mg, 254 μmol) with 4-bromobenzonitrile (61.3 mg, 330 μmol) yielded the 3′-((R)-3-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-5-yl)-4′-fluoro-biphenyl-4-carbonitrile (137 mg, 78% yield) as a white foam. MS (ISP): m/z=690.4 [M+H]+.

Sources & evidence

ORD record
ord-d255f51f96c44c04a32bf5ceabbfb418
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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