5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 118195117, compound

HRID 924022Notes

Reaction equation

HRID 924022 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][CH:39]=[C:40]([CH:43]=2)[C:41]#[N:42])O1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:6]2[CH:21]=[C:2]([C:36]3[CH:37]=[N:38][CH:39]=[C:40]([C:41]#[N:42])[CH:43]=3)[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=2)=[O:8])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 72545856(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195117HCID 118195117, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a white solid. UPLC-MS (Condition 3) tR=1.02 min, m/z=486.2 [M+H]+, m/z=530.0 [M+ formic acid-H]; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.80 (m, 1H) 1.80-1.91 (m, 1H) 2.85 (d, J=11.42 Hz, 1H) 3.16-3.26 (m, 2H) 3.35-3.43 (m, 1H) 4.20 (br. s, 1H) 4.90 (d, J=3.64 Hz, 1H) 7.35 (d, J=9.16 Hz, 2H) 7.82-7.89 (m, 2H) 8.10 (d, J=2.38 Hz, 1H) 8.41 (t, J=2.07 Hz, 1H) 8.79 (d, J=2.38 Hz, 1H) 8.90 (d, J=2.26 Hz, 1H) 9.03 (d, J=1.88 Hz, 1H) 10.20 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-a94e542fa13349e6a29dada95ae088d7
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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