2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile → HCID 118195146, compound

HRID 924160Notes

Reaction equation

HRID 924160 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].[CH3:28][O:29][C:30]1[N:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:31]=1[C:32]#[N:33]>>[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:35]3[CH:36]=[N:37][C:30]([O:29][CH3:28])=[C:31]([C:32]#[N:33])[CH:34]=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 467391362-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrileHCID 72545856(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195146HCID 118195146, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 298 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1) and 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford an off-white powder. UPLC-MS (Condition 11), tR=1.13 min, m/z=516.2/518.2 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.67-1.78 (m, 1H) 1.79-1.93 (m, 1H) 2.90 (d, J=11.29 Hz, 1H) 3.19-3.29 (m, 2H) 3.35-3.43 (m, 1H) 4.06 (s, 3H) 4.21 (br. s, 1H) 4.90 (br. s, 1H) 7.33 (d, J=8.66 Hz, 2H) 7.85 (d, J=8.85 Hz, 2H) 8.02 (d, J=1.88 Hz, 1H) 8.35 (s, 1H) 8.50 (s, 1H) 8.77 (d, J=1.88 Hz, 1H) 10.18 (s, 1H).

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-d0c467a88ccd4f4091fc88d1949a7718
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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