5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 68774417, compound

HRID 1175618Notes

Reaction equation

HRID 1175618 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][CH:29]=[C:30]([CH:33]=2)[C:31]#[N:32])O1>>[C:31]([C:30]1[CH:33]=[C:26]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:6][N:7]=2)[CH:27]=[N:28][CH:29]=1)#[N:32]

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 86609792HCID 86609792, compound

Product 1

HCID 68774417HCID 68774417, compoundYield 47%

Procedure

Prepared in a similar manner to Example 23 from 2-(6-bromopyridin-3-yl)-N-isobutyl-2-methylpropanamide (example 40a) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile. Yield: 47%. 1H NMR (400 MHz, dMSO): δ 0.72-0.74 (d, 6H), 1.51 (s, 6H), 1.66-1.69 (m, 1H), 2.82-2.86 (m, 2H), 7.62-7.64 (m, 1H), 7.82-7.85 (m, 1H), 8.10-8.12 (d, 1H), 8.65-8.66 (d, 1H), 8.89-8.90 (t,1H), 9.05-9.06 (d, 1H), 9.50-9.51 (d, 1H); MS+H (323).

Sources & evidence

ORD record
ord-2e634a86f5ee4d8c85bcaf96f0a2b002
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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