3-Cyanophenylboronic acid → HCID 71059427, compound

HRID 1525179Notes

Reaction equation

HRID 1525179 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C@:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C@@:5]12[C:21]([F:23])([F:22])[CH2:20][O:19][C:18]([NH2:24])=[N:17]1.[C:25]([C:27]1[CH:28]=[C:29](B(O)[OH:34])[CH:30]=[CH:31][CH:32]=1)#[N:26]>>[CH:20]([OH:19])=[O:34].[NH2:24][C:18]1[O:19][CH2:20][C:21]([F:23])([F:22])[C@:5]2([N:17]=1)[C:4]1[C:14](=[CH:15][CH:16]=[C:2]([C:31]3[CH:32]=[C:27]([CH:28]=[CH:29][CH:30]=3)[C:25]#[N:26])[CH:3]=1)[O:13][C@:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6]2

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 71059508HCID 71059508, compound

Product 1

HCID 71059427HCID 71059427, compoundYield 25%

Procedure

In a manner analogous to that described in Example 19, the cross coupling reaction of (2′R,4R)-6′-bromo-5,5-difluoro-5,5″,6,6″-tetrahydro-4″H-dispiro[1,3-oxazine-4,4′-chromene-2′,3″-pyran]-2-amine (intermediate B6.7) with 3-cyanophenylboronic acid and chromatography on preparative HPLC yielded the title compound (25% yield) as a pale yellow solid. MS (ISP): m/z=426.2 [M+H]+.

Sources & evidence

ORD record
ord-d8d809d5a4a846a19e3477bc4043f12d
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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