5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 118195184, compound

HRID 924076Notes

Reaction equation

HRID 924076 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][CH:41]=[C:42]([CH:45]=2)[C:43]#[N:44])O1>>[C:43]([C:42]1[CH:45]=[C:38]([C:2]2[C:3]([N:24]3[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=3)=[O:8])[CH:23]=2)[CH:39]=[N:40][CH:41]=1)#[N:44]

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 86702613HCID 86702613, compound

Product 1

HCID 118195184HCID 118195184, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethyl)phenyl)nicotinamide (Stage 208.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.08 min, m/z=504.4 [M+H]+, m/z=502.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.80 (m, 1H) 1.80-1.92 (m, 1H) 2.86 (d, J=11.25 Hz, 1H) 3.16-3.28 (m, 2H) 3.39 (m, J=9.29 Hz, 1H) 4.21 (br. s, 1H) 4.89 (d, J=3.18 Hz, 1H) 7.67 (d, J=8.80 Hz, 2H) 8.01 (d, J=8.56 Hz, 2H) 8.11 (d, J=2.20 Hz, 1H) 8.38-8.43 (m, 1H) 8.81 (d, J=2.20 Hz, 1H) 8.91 (d, J=1.96 Hz, 1H) 9.03 (d, J=1.96 Hz, 1H) 10.34 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-a4cbe59d795946c6a29045d4615d79da
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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