5-Chloropyridine-3-boronic acid → HCID 71059559, compound

HRID 1525178Notes

Reaction equation

HRID 1525178 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.[Cl:25][C:26]1[CH:27]=[C:28](B(O)[OH:33])[CH:29]=[N:30][CH:31]=1>>[CH:20]([OH:19])=[O:33].[Cl:25][C:26]1[CH:27]=[C:28]([C:2]2[CH:3]=[C:4]3[C:14](=[CH:15][CH:16]=2)[O:13][C@:7]2([CH2:12][CH2:11][CH2:10][O:9][CH2:8]2)[CH2:6][C@@:5]23[C:21]([F:23])([F:22])[CH2:20][O:19][C:18]([NH2:24])=[N:17]2)[CH:29]=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 71059508HCID 71059508, compound

Product 1

HCID 71059559HCID 71059559, compoundYield 66%

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 5-chloropyridin-3-ylboronic acid and chromatography on preparative HPLC yielded the title compound (66% yield) as an off-white, amorphous material. MS (ISP): m/z=436 [M+H]+ and 438 [M+2+H]+.

Sources & evidence

ORD record
ord-df8d8fd5e609420c91a3ea48cd927701
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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