3-Pyridinylboronic acid → 2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinyl)-2-pyrimidinyl]-1H-benzimidazole

HRID 450186Notes

Reaction equation

HRID 450186 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:23]([F:25])[F:24])[N:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>>[F:24][CH:23]([F:25])[C:15]1[N:14]([C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:7]=[C:2]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)[N:3]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 442492591-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-1H-benzimidazole

Product 1

HCID 498697802-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinyl)-2-pyrimidinyl]-1H-benzimidazoleYield 77%

Procedure

Using a similar procedure to Example 47, reaction of 1-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-1H-benzimidazole (International Publ. No. WO 2008/032028, the disclosure of which is incorporated herein by reference in its entirety) and 3-pyridinylboronic acid gave 2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(3-pyridinyl)-2-pyrimidinyl]-1H-benzimidazole in 77% yield: mp (CH2Cl2/hexanes) 172-179° C.; 1H NMR (DMSO-d6) δ 9.44 (d, J=2.2 Hz, 1H), 8.75 (dd, J=4.8, 1.5 Hz, 1H), 8.61 and 8.59 (2m, 1H), 8.39 (d, J=8.20 Hz, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.82 (t, JHF=52.8 Hz, 1H), 7.62 (dd, J=8.0, 4.8 Hz, 1H), 7.55-7.51 (m, 2H), 7.46-7.42 (m, 1H), 3.88-3.84 (m, 4H), 3.79-3.77 (m, 4H); Anal. Calcd. for C21H18F2N6O1.9H2O: C, 49.1; H, 4.8; N, 15.6. Found: C, 49.0; H, 4.4; N, 15.0%

Sources & evidence

ORD record
ord-52200d37520d4b269a861427b1eb0f15
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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