5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 118195384, compound

HRID 924071Notes

Reaction equation

HRID 924071 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][CH:40]=[C:41]([CH:44]=2)[C:42]#[N:43])O1>>[C:42]([C:41]1[CH:44]=[C:37]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16][C:17]([F:18])([F:19])[F:20])=[C:12]([F:21])[CH:11]=3)=[O:8])[CH:22]=2)[CH:38]=[N:39][CH:40]=1)#[N:43]

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 86702610(R)-5-bromo-N-(3-fluoro-4-((trifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195384HCID 118195384, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-N-(3-fluoro-4-((trifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 205.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.10 min, m/z=504.3 [M+H]+, m/z=502.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.78 (m, 1H) 1.83 (dd, J=8.72, 4.33 Hz, 1H) 2.84 (d, J=11.29 Hz, 1H) 3.13-3.25 (m, 2H) 3.34-3.41 (m, 1H) 4.14-4.24 (m, 1H) 4.87 (d, J=3.51 Hz, 1H) 7.65 (dd, J=8.91, 1.88 Hz, 1H) 7.74 (t, J=8.16 Hz, 1H) 7.95 (dd, J=11.80, 2.13 Hz, 1H) 8.07 (d, J=2.38 Hz, 1H) 8.38 (t, J=2.07 Hz, 1H) 8.78 (d, J=2.26 Hz, 1H) 8.88 (d, J=2.13 Hz, 1H) 9.01 (d, J=2.01 Hz, 1H) 10.43 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-1ffa79fc4a764911ab287dcd308bd638
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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