5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 71059401, compound

HRID 1525150Notes

Reaction equation

HRID 1525150 reaction equation
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][CH2:7][CH2:8][C@@:9]32[C:14]([F:16])([F:15])[CH2:13][O:12][C:11]([NH2:17])=[N:10]3)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[N:30][CH:31]=[C:32]([CH:35]=2)[C:33]#[N:34])O1>>[NH2:17][C:11]1[O:12][CH2:13][C:14]([F:16])([F:15])[C@@:9]2([C:18]3[C:5](=[CH:4][CH:3]=[C:2]([C:28]4[CH:29]=[N:30][CH:31]=[C:32]([CH:35]=4)[C:33]#[N:34])[CH:19]=3)[CH2:6][CH2:7][CH2:8]2)[N:10]=1

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 71059628HCID 71059628, compound

Product 1

HCID 71059401HCID 71059401, compoundYield 72%

Procedure

In a manner analogous to that described in Example 1, the cross-coupling reaction of (R)-7-bromo-5′,5′-difluoro-3,4,5′,6′-tetrahydro-2H-spiro[naphthalene-1,4′-[1,3]oxazin]-2′-amine (intermediate A6.1) with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile yielded the title compound (72% yield) as an off-white solid. MS (ISP): m/z=355.2 [M+H]+.

Sources & evidence

ORD record
ord-bf402dbb9bf1476daecb12d9e6d768e1
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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