5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 68775072, compound

HRID 1175625Notes

Reaction equation

HRID 1175625 reaction equation
Br[C:2]1[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])=[N:6][CH:7]=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:7]=[N: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]=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 68778103HCID 68778103, compound

Product 1

HCID 68775072HCID 68775072, compoundYield 49%

Procedure

Prepared in a similar manner to Example 23 from 2-(5-bromopyridin-2-yl)-N-isobutyl-2-methylpropanamide (example 42a) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile. Yield 49%. 1H NMR (400 MHz, acetonitrile-d6): δ 0.80-0.81 (d, 6H), 1.63 (s, 6H), 1.71-1.77 (m, 1H), 2.97-3.00 (t, 2H), 7.01 (bs, 1H), 7.59-7.62 (d, 1H), 8.18-8.21 (dd, 1H), 8.59-8.60 (t, 1H), 8.99 (d, 1H), 9.20-9.21 (d, 1H); MS+H (323).

Sources & evidence

ORD record
ord-f99234d7279845989efaa51f8f68c274
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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