(Pyrimidin-5-yl)boronic acid → HCID 71059742, compound

HRID 1525171Notes

Reaction equation

HRID 1525171 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[N:20]1[CH:25]=[C:24](B(O)O)[CH:23]=[N:22][CH:21]=1>>[F:17][C:16]1([F:18])[CH2:15][O:14][C:13]([NH2:19])=[N:12][C@@:11]21[C:4]1[C:5](=[CH:6][CH:7]=[C:2]([C:24]3[CH:25]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:3]=1)[O:8][CH2:9][CH2:10]2

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 71059632HCID 71059632, compound

Product 1

HCID 71059742HCID 71059742, compoundYield 55%

Procedure

In a manner analogous to that described in Example 19, the cross coupling reaction of (R)-6-bromo-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[1,3]oxazin]-2′-amine (intermediate B6.1) with pyrimidin-5-ylboronic acid yielded the title compound (55% yield) as a pale yellow solid. MS (ISP): m/z=333.1 [M+H]+.

Sources & evidence

ORD record
ord-257a31c1a7664838805e720051342dd1
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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