1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 118075947, compound

HRID 1051621Notes

Reaction equation

HRID 1051621 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C@H:7]([CH3:13])[NH:8]2.[CH:14]1([N:17]2[CH:21]=[C:20](B3OC(C)(C)C(C)(C)O3)[CH:19]=[N:18]2)[CH2:16][CH2:15]1>>[C:3]([N:8]1[C:9]2[C:4](=[C:3]([O:2][C:1]3[CH:10]=[CH:9][CH:4]=[CH:5][C:6]=3[C:7]#[N:8])[C:12]([C:20]3[CH:19]=[N:18][N:17]([CH:14]4[CH2:15][CH2:16]4)[CH:21]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:6][C@@H:7]1[CH3:13])(=[O:2])[CH3:12]

Participants

3

Reactant 2

HCID 593271331-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 118075405(S)-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 118075947HCID 118075947, compound

Procedure

(S)-2-(1-acetyl-6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-1,2,3,4-tetrahydroquinolin-5-yloxy)benzonitrile was synthesized according to the procedures described above for Example 36, with the following changes: (1) in Step 2, 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole was used in place of tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (3) Step 3 (removal of the Boc-protecting group) was eliminated. 1H NMR (300 MHz, CD3OD) δ ppm 0.92-1.05 (m, 4H), 1.16 (d, J=6.30 Hz, 3H), 1.35-1.52 (m, 1H), 2.10-2.40 (m, 5H), 2.58-2.80 (m, 1H), 3.55-3.65 (m, 1H), 4.68-4.8 9 (m, 1H), 6.40-6.55 (m, 1H), 7.05-7.15 (m, 1H), 7.30-7.52 (m, 2H), 7.55-7.65 (m, 1H), 7.70-7.80 (m, 2H), 7.96 (s, 1H). MS (ESI, pos. ion) m/z 413 [M+H]+.

Workup

  1. customremoval of the Boc-

Sources & evidence

ORD record
ord-1d4ff843a9f04bbf926b1ae4d4dfd66b
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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