Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-(7-fluoro-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1025500Notes

Reaction equation

HRID 1025500 reaction equation
BrC1C=C(F)C2OC(C3CCN(C4N=CC(CCC)=CN=4)CC3)CC=2C=1.CC1(C)C(C)(C)OB(C2CCN(C(OC(C)(C)C)=O)CC=2)O1.[F:49][C:50]1[C:58]2[O:57][CH:56]([C:59]3(O)[CH2:64][CH2:63][N:62]([C:65]4[N:70]=[CH:69][C:68]([CH2:71][CH2:72][CH3:73])=[CH:67][N:66]=4)[CH2:61][CH2:60]3)[CH2:55][C:54]=2[CH:53]=[C:52]([C:75]2[CH2:80][CH2:79][N:78]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:77][CH:76]=2)[CH:51]=1>>[F:49][C:50]1[C:58]2[O:57][CH:56]([CH:59]3[CH2:60][CH2:61][N:62]([C:65]4[N:70]=[CH:69][C:68]([CH2:71][CH2:72][CH3:73])=[CH:67][N:66]=4)[CH2:63][CH2:64]3)[CH2:55][C:54]=2[CH:53]=[C:52]([C:75]2[CH2:80][CH2:79][N:78]([C:81]([O:83][C:84]([CH3:85])([CH3:87])[CH3:86])=[O:82])[CH2:77][CH:76]=2)[CH:51]=1

Participants

4

Reactant 3

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 67468836tert-Butyl 4-(7-fluoro-2-(4-hydroxy-1-(5-propylpyrimidin-2-yl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridine-1(2H)-carboxylateHCID 682115302-(4-(5-Bromo-7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-propylpyrimidine

Product 1

HCID 68211505tert-Butyl 4-(7-fluoro-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

Compound 3G was prepared from Compound 3F and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate in a similar manner to the procedure described for Compound 1I in Example 1. 1H NMR (500 MHz, CDCl3) δ ppm 8.15 (s, 2 H), 6.96 (s, 1 H), 6.92 (d, J=12.1 Hz, 1 H), 5.91 (br. s., 1 H), 4.81 (dd, J=13.3, 1.2 Hz, 2 H), 4.61-4.71 (m, 1 H), 4.04 (d, J=1.9 Hz, 2H), 3.61 (t, J=5.6 Hz, 2 H), 3.24 (dd, J=15.7, 9.1 Hz, 1 H), 3.04 (dd, J=15.7, 8.3 Hz, 1 H), 2.78-2.91 (m, J=12.8, 12.8, 6.1, 2.8 Hz, 2 H), 2.34-2.50 (m, 4 H), 2.01-2.09 (m, 1 H), 1.91-2.01 (m, 1 H), 1.70-1.79 (m, 1 H), 1.53-1.62 (m, 2 H), 1.49 (s, 9 H), 1.32-1.44 (m, 2 H), 0.93 (t, J=7.3 Hz, 3 H). 19F NMR (471 MHz, CDCl3) δ ppm −138.98. LC/MS (m/z)=523 (M+H)+.

Sources & evidence

ORD record
ord-3121e147c2b5418bb5566ff6e152106d
Source dataset
uspto-grants-2014_05
Patent number
US08729084B2

Reaction notes

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