4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole → (R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(isoxazol-4-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 525649Notes

Reaction equation

HRID 525649 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]([F: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][O:39][CH:40]=2)O1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:36]3[CH:37]=[N:38][O:39][CH:40]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 164141804-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazoleHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89908216(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(isoxazol-4-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 7 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 6.1) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole to afford a white solid. LC-MS (Condition 2) tR=1.80 min, m/z=435.2-436.2 [M+H]+, m/z=433 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.74-1.82 (m, 1H) 1.84-1.94 (m, 1H) 3.01 (d, J=11.25 Hz, 1H) 3.29-3.53 (m, 3H) 4.22-4.28 (m, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.86 (d, J=9.05 Hz, 2H) 8.03 (d, J=2.20 Hz, 1H) 8.75 (d, J=2.20 Hz, 1H) 8.85 (s, 1H) 9.12 (s, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-7b3258af23f243b584ab5a92733842cf
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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